1.1: A 3 L three-necked round bottom flask equipped with mechanical stirrer (or magnetic stirrer), addition funnel and thermometer (or Dean-Stock; drying tube)1.2: All flasks used in the reaction were heated under vacuum for 30 minutes and purged with N2 for 10 minutes. (無水反應裝置)2.1.1: A 3 L three-necked round bottom flask equipped with mechanical stirrer (or magnetic stirrer), addition funnel and thermometer (or Dean-Stock; drying tube) were charged with A(10 mL, 1 mole), B (2 g, mole) and C (50 mL),2.1.1.1: a solution of D (10 g, 1 mole) in E (20 mL) was added dropwise (via addition funnel or syringe) at 10oC (or while maintaining gentle reflux; while keeping inner temperature between 10oC –30oC) under N2 （液體滴加到反應液中）2.1.1.2: D (10 g, 1 mole) was added in portions during a period of 1 hr (固體分批加入到反應液中)2.1.1.3: D (10 g, 1 mole) and E (20 mL) were added in turn.2.2: To a solution (mixture, suspension or slurry) of A (10 mL, 1 mole) and B (2 g, mole) in C (50 mL)2.2.1: was added dropwise a solution of D (10 g, 1mole) in E (20 mL) with stirring at 10oC (or while maintaining gentle reflux; while keeping inner temperature between 10oC – 30oC) under N22.2.2: was added D (10 g, 1 mole) in portions duringa period of 1 hr2.2.3: were added D (10 g, 1 mole) and E (20 mL) in turn2.3.1: A solution of D (10 g, 1 mole) in E (20 mL)was added dropwise into a solution (mixture or suspension) of A (10 mL, 1mole) and B (2 g, mole) in C (50 mL) at 10oC (or while maintaining gentle reflux; while keeping inner temperature between 10oC – 30oC) under N2.2.3.2: D (10 g, 1 mole) was added into a solution(mixture or suspension) of A (10 mL, 1 mole) and B (2 g, mole) in C (50mL) in portions2.3.3: D (10 g, 1 mole) and E (20 mL) were added into a solution (mixture or suspension) of A (10 mL, 1 mole) and B (2 g,mole) in C (50 mL) in turn2.4.1: A solution of BuLi or BH3/THF (10 mL, 1 mole,2.5 M in hexane) was cannulated into addition funnel or into a solution A in solvent B2.4.2: A solution of BuLi or BH3/THF (10 mL, 1 mole,2.5 M in hexane) was added into a solution of A in solvent B via cannula, dropping funnel or syringe over a period of hrsA (1 g, 1 mol) and B (1 g, 1 mol) were dissolved insolvent C, evaporated to dryness and heated for x hours at x oCA (20 mL, 142 mmol) and catalytic amount (a traceamount or two drops) of B were added into a solution of C (4.549 g, 46.4mmol) in D(120mL) at 0 oCA solution of A (x g, x mol) in methanol (x mL) saturated with NH3 (or other gas such as: CO, CO2, H2S) was stirred under 50 Psi at x oC for x hours in a 50 mL of sealed tube or autoclave.3.4.1: A solution of A (x g, x mol) in methanol (xmL) saturated with HCl was stirred at x ℃.3.4.2: Ozone was bubbled into a solution of A (x g,x mol) in MeOH (x mL) at x oC for 15 minutes. After excess O3 was purged by N2, Me2S (x mL) was added at x oC.3.4.3: Gas was bubbled into a solution of A (x g, xmol) and B (x g, x mol) in solvent C (x mL) at x oC for x hours.3.5.1: To a solution of A (x g, x mol) in a mixture of solvent B (mL) and solvent C (x mL) (or a mixed solvent of B and C) was added D (x g, x mol) at x oC, the reaction mixture was allowed to stir(reflux or heat) for x hrs.3.5.2: To a solution of A (x g, x mol) in 10: 1 aqueous acetone (x mL) was added B (x g, x mol) followed by addition of C(x g, x mol), the reaction mixture was allowed to stir (reflux or heat) for x hrs.3.6.1: A (x g, x mol) and B (x g, x mol) in benzene or toluene (x mL) were refluxed for x hours with azeotropical removal of water.3.6.2; A mixture of A, B and TsOH.H2O (56.91 g, 0.3mol) in toluene (400 mL) was heated to reflux and remove water by Dean-Stark trap. To a solution of A (x g, x mol) in EtOH (x mL) was added Pd-C or Ra-Ni or Pd(OH)2/C (10%, x g) under N2. The suspension was degassed under vacuum and purged with H2 several times.3.7.1: The mixture was stirred under H2 (x psi) at x℃ for x hours. [氫化瓶或高壓釜]3.7.2: The mixture was stirred under H2 balloon at x℃ for x hours. [常壓氫化如氣球反應]3.7.3: A mixture of A (x g, x mol) and Ra-Ni (x g)in EtOH (x mL) was hydrogenated under 50 Psi of hydrogen pressure for xhours at room temperature.4.1: The reaction mixture (solution or suspension) was stirred at 5oC for 2 hrs and then kept at room temperature (or ambienttemperature) for another 2 hrs (or overnight)4.2: The reaction mixture (solution or suspension) was refluxed (heated to reflux) or heated at 60oC for 2 hrs (or overnight)4.3: The reaction mixture (solution or suspension)was allowed to reflux (or heat to reflux) for 2 hrs (or overnight)4.4: The reaction mixture (solution or suspension)was allowed to warm to temperature during 2 hrs and reflux (or heat toreflux) for 2 hrs (or overnight)5.1: Taking sample from the reaction mixture(solution or suspension) by dropping tube or syringe. After workup, check the reaction via TLC, LC-MS or HPLC etc.. (預處理)5.2.1: The reaction was complete (incomplete or messy) detected (determined or confirmed) by TLC (PE/EtOAc 4:1), LC-MS,HPLC or NMR5.2.2: TLC (PE:EtOAc=1:1) or HPLC (107757-088-1)showed or indicated that the reaction was complete.5.2.3: TLC (PE:EtOAc=1:1) or HPLC (107757-088-1)showed the starting material was consumed completely.5.2.4: TLC (PE:EA=1:1) or HPLC (107757-088-1) showed the reaction didn’t work at all or most of starting material was still remained.5.2.5: The starting material was consumed completely, but no desired compound was detected or determined by MS(106657-078-1) or LC-MS (106657-078-1).5.2.6: Several spots were shown on TLC.5.2.7: Only a trace amount of desired compound was detected by MS (106657-078-1) or LC-MS (106657-078-1) or HPLC(106657-078-1) or TLC (PE:EtOAc=1:1).5.2.8: The desired compound could not be isolated, separated or purified by chromatography or prep. HPLC due to poor yield or poor solubility.5.2.9:1H NMR (106675-010-2) or MS confirmed the obtained (or isolated) compound is not the desired compound. The reaction was failed.6.1: An aqueous solution of A (10 mL) was added dropwise into the reaction mixture once the reaction mixture (solution orsuspension) was allowed to warm (or cool) to -5oC or room temperature(ambient temperature).6.2: The hot (or cold) reaction mixture (solution orsuspension) was poured into water (ice water) or poured onto ice.6.3: The reaction mixture (solution or suspension) was concentrated (distilled) under reduced pressure (in vacuum) or evaporated to remove MeOH (THF; DMF etc.) or excess SOCl2 (reagent). Then the reaction residue (or the residual) was diluted with solvent and poured into water (ice water) or poured onto ice.7.1: The residue was partitioned between ethylacetate (100 mL) and 1N aq. HCl (50 mL). The separated organic layer was washed with water, dried over (Na2SO4 or MgSO4) and evaporated to dryness.7.2: After quenching the reaction, the reaction mixture was poured into separatory funnel and separated.7.3: The aqueous layer (or phase) was extracted with organic solvent (40 mL) twice (or X times). The combined organic layers were (or the organic layers were combined and) washed with an aqueous solution of A (50 mL) or water and dried over Na2SO4 or MgSO4.7.4: The combined aqueous layers were extracted with solvent (40 mL) twice (or X times) to remove neutral impurities. The aqueous phase was acidified (or basified) with aqueous HCl (or NaHCO3) till PH = X and extracted with organic solvent.7.5: The combined organic layers were (or theorganic layers were combined and) washed with an aqueous solution of A (50mL) or water and dried over Na2SO4 or MgSO4.8.1: After filtration via filter paper or Celitepad, the organic layer (or extract) was concentrated under reduced pressure (or in vacuum) or evaporated to dryness to provide (afford; giveor yield) an oil (or foam) (which solidified on standing) or a white solid.8.2: The organic layer (or extract) was filtered and concentrated under reduced pressure (or in vacuum) or evaporated to dryness to provide (afford or give) A (10 g, 0.5 mole) an oil (or foam)(which solidified on standing) or a white solid.8.3: After removal of solvent by evaporation or concentration, A (10 g, 0.5 mole) was obtained (or prepared) an oil (orfoam) (which solidified on standing) or a white solid.8.4: The extract in CH2Cl2 was evaporated to dryness and then swapped with toluene to remove residual CH2Cl2.9.1: The reaction mixture or solution was concentrated to dryness. [適用於反應液不需要quench]9.2: After the reaction mixture was cooled to 0 ℃, the reaction mixture was quenched by addition of xmL of H2O, followed by x mL of 15% aqueous NaOH. After being stirred at room temperature for x hour, the solid was removed by filtration (orthe mixture was filtered)through Celite pad to remove by-product). The filtrate was concentrated to dryness to give crude product. [LiAlH4 反應的經典後處理]9.3: The mixture was diluted with water (x mL), neutralized with solid K2CO3 until no CO2 was evolved. [適用於酸性反應液的後處理]9.4: The suspension was filtered through a pad of Celite or silica gel and the pad or filter cake was washed with EtOH (xmL×x). The combined filtrates were concentrated to dryness to give product(x g, x%) as. [適用氫化反應的後處理, 或者難於過濾的反應液的後處理, 但要注意的是這裡需要的是濾液而不是固體才能添加助濾劑]9.5: The reaction mixture was poured into x mL of ice-water carefully and the organic layer or phase was separated. [產物在有機相裡]9.6: The reaction mixture was poured into x mL of ice-water carefully and the aqueous phase was washed with Et2O (x mL×x) [產品在水相] and acidified with 1NHCl to pH=3. The resulting precipitate was collected by filtration or the resulting solution was extracted with EA9.7: The reaction mixture was filtered and the filter cake was washed with x mL of solvent, dried in vacuum to give or afford product. [這裡需要的是固體而不是濾液]9.8: The reaction mixture was quenched with x mL of saturated aqueous NH4Cl. The resulting solution was extracted with EA (xmL×x). [適用於丁基鋰等活潑金屬有機物的後處理]9.10: The residue was triturated with ether and filtered to afford a white solid. (磨碎)9.11: The crude product was purified by prep. HPLC to give A as a colorless thick oil which was solidified on standing. (靜止固化)9.12: After prep. HPLC purification, the eluent was concentrated or evaporated to remove organic solvents. The residual aqueous solution was lyophilized to give a white solid. (冷凍乾燥)9.13: After concentration, the crude product was used directly for the next step without purification.10.1: The crude product was purified by silica gel chromatography eluted with PE: EtOAc=10:1 to give product (x g, x%) as yellow solid.10.2: The crude product was purified by recrystallization (or recrystallized) from x solvent (x mL).10.3: The crude product was distilled in vacuum (xoC, x pressure) to afford pure product (x g, x%) as colorless liquid.10.4: The crude product was pre-purified by column chromatography followed by prep. HPLC purification or re-crystallization to afford pure product.
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