The chemical industry reduces the impact on the environment during synthesis 558-42-9, I believe this compound will play a more active role in future production and life.
Electric Literature of 558-42-9, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.558-42-9, name is 1-Chloro-2-methyl-2-propanol, molecular formula is C4H9ClO, molecular weight is 108.5667, as common compound, the synthetic route is as follows.
To a solution of 4-hydroxy-3,5-dimethylbenzonitrile (2.00 g, 13.5 mmol) and 1-chloro-2-methyl propan-2-ol (8.85 g, 81.5 mmol) in ethanol (50 mL) was added potassium carbonate (7.5 g, 54 mmol) and water (5 mL). The reaction EPO mixture was stirred at reflux for 24 hours. Cooled to room temperature. The precipitated solid was filtered off and washed with water. The solid was dissolved in ethyl acetate (100 mL), washed with water (50 mL), brine (50 ml_) and dried over anhydrous Na2SO4. Removal of solvent gave 4-(2-hydroxy-2- methylpropoxy)-3,5-dimethyl benzonitrile (2.9 g, 97percent) as a white solid. To a solution of 4-(2-hydroxy-2-methylpropoxy)-3,5-dimethyl benzonitrile (2.90 g, 13.2 mmol) in anhydrous DMF (20 mL) was added imidazole (2.7 g, 40 mmol) and tert- butyldimethylsilylchloride (2.19 g, 14.6 mmol). The reaction mixture was stirred at room temperature under nitrogen for 3 days. Water (200 mL) was added and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed with water (2×100 mL) and brine (100 mL), and dried over anhydrous Na2SO4. The solventwas removed under reduced pressure and the crude compound was purified by column chromatography (Silica Gel 230-400 mesh; 10percent ethyl acetate in hexanes as eluent) to give 4-[2-(te/?-butyldimethylsilanyloxy)-2-methylpropoxy]- 3,5-dimethylbenzonitrile (2.24 g, 54percent). n-Butyl lithium (6.2 mL, 6.6 mmol, 1.6 M solution in hexanes) was added to a solution of 2,4-dimethoxy-6-/V- dimethylbenzamide (0.9 g, 4.3 mmol) in anhydrous THF (10 mL) dropwise at – 1O0C over a period of 10 min under nitrogen. The stirring was continued at O0C for 1 hour. The reaction mixture was cooled to -5O0C. A solution of 4-[2-(tert- butyldimethylsilanyloxy)-2-methylpropoxy]-3,5-dimethylbenzonitrile (1.58 g, 4.73 mmol) in anhydrous THF (5 mL) was quickly added. The cooling bath was removed and the reaction mixture was allowed to warm to room temperature. The stirring was continued at room temperature for 1 hour. Aqueous ammonium chloride solution (10 mL) was added. Ethyl acetate (100 mL) was added. The organic layer was separated, washed with water (10 mL) and dried (Na2SO4). The solvent was removed under reduced pressure and the crude compound was purified by column chromatography (Silica Gel 230-400 mesh; 0-5percent methanol in CH2CI2 as eluent) to give 3-{4-[2-(terf-butyldimethylsilanyloxy)-2-methylpropoxy]- 3,5-dimethylphenyl}-6,8-dimethoxy-2H-isoquinolin-1-one (0.82 g, 37percent) of as white solid. The above compound (0.42 g, 0.82 mmol) was dissolved in anhydrous THF (20 mL). Tetrabutyl ammonium fluoride (4.1 mL, 1.0M solution in THF) was added at O0C. The reaction mixture was stirred at O0C for 10 min, then at room temperature for 2 h and then stirred at 7O0C for 24 hours. The mixture was cooled EPO to room temperature. Saturated aqueous ammonium chloride (30 ml_) was added. The organic phase was separated, washed with water, brine and dried over anhydrous Na2SO4. The solvent was removed under reduced pressure. The crude product was purified by column chromatography (Silica Gel 230-400 mesh; 0-4percent methanol in CH2CI2 as eluent) to give 3-(4-(2-hydroxy-2-methylpropoxy)-3,5- dimethylphenyl)-6,8-dimethoxyisoquinolin-1(2H)-one (0.15 g, 46percent) as a white solid. MS (ES) m/z: 398.96 (M+1 ); MP 252-2540C
The chemical industry reduces the impact on the environment during synthesis 558-42-9, I believe this compound will play a more active role in future production and life.
Reference:
Patent; RESVERLOGIX CORP.; JOHANSSON, Jan, O.; HANSEN, Henrik, C.; CHIACCHIA, Fabrizio, S.; WONG, Norman, C.W.; WO2007/16525; (2007); A2;,
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