甲基 4-(2,2-二甲氧基乙基)苯甲酸甲酯

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a cooled (−78° C.) solution of methyl 4-(2,2-dimethoxyethyl)benzoate (assume 7.08 mmol) in THF (30 mL) was added drop wise a solution of lithium aluminium hydride (2.0 M in THF, 3.50 mL, 7.00 mmol). The reaction mixture was allowed to warm to RT over 4 hours. The mixture was sequentially treated with water (0.266 mL), 2M aqueous sodium hydroxide (0.266 mL) and water (3×0.266 mL). The mixture was diluted with ethyl acetate and magnesium sulfate added. The mixture was stirred at RT for 1 hour and then filtered through celite. The filter cake was washed with further ethyl acetate and the filtrates combined. The solvent was evaporated at reduced pressure and the residue was purified by flash column chromatography eluting with 0-30% ethyl acetate in iso-hexane to afford the title compound (0.854 g, 62%). added filtered through celite The filter cake was washed with further ethyl acetate The solvent was evaporated at reduced pressure the residue was purified by flash column chromatography eluting with 0-30% ethyl acetate in iso-hexane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a cooled (−78° C.) solution of methyl 4-(2,2-dimethoxyethyl)benzoate (assume 7.08 mmol) in THF (30 mL) was added drop wise a solution of lithium aluminium hydride (2.0 M in THF, 3.50 mL, 7.00 mmol). The reaction mixture was allowed to warm to RT over 4 hours. The mixture was sequentially treated with water (0.266 mL), 2M aqueous sodium hydroxide (0.266 mL) and water (3×0.266 mL). The mixture was diluted with ethyl acetate and magnesium sulfate added. The mixture was stirred at RT for 1 hour and then filtered through celite. The filter cake was washed with further ethyl acetate and the filtrates combined. The solvent was evaporated at reduced pressure and the residue was purified by flash column chromatography eluting with 0-30% ethyl acetate in iso-hexane to afford the title compound (0.854 g, 62%). added filtered through celite The filter cake was washed with further ethyl acetate The solvent was evaporated at reduced pressure the residue was purified by flash column chromatography eluting with 0-30% ethyl acetate in iso-hexane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of methyl 4-(2-methoxyvinyl)benzoate (1.36 g, 7.08 mmol) in methanol (30 mL) was added para-toluenesulfonic acid monohydrate (pTSA) (0.135 g, 0.71 mmol) and the reaction mixture heated under reflux for 18 hours. The solvent was evaporated at reduced pressure. The residue was partitioned between DCM and 10% aqueous potassium carbonate. The organic phase was poured through a hydrophobic fit and the solvent evaporated at reduced pressure. The crude material was used in the next step without further purification. the reaction mixture heated under reflux for 18 hours The solvent was evaporated at reduced pressure The residue was partitioned between DCM and 10% aqueous potassium carbonate The organic phase was poured through a hydrophobic fit the solvent evaporated at reduced pressure The crude material was used in the next step without further purification

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a cooled (−78° C.) solution of methyl 4-(2,2-dimethoxyethyl)benzoate (assume 7.08 mmol) in THF (30 mL) was added drop wise a solution of lithium aluminium hydride (2.0 M in THF, 3.50 mL, 7.00 mmol). The reaction mixture was allowed to warm to RT over 4 hours. The mixture was sequentially treated with water (0.266 mL), 2M aqueous sodium hydroxide (0.266 mL) and water (3×0.266 mL). The mixture was diluted with ethyl acetate and magnesium sulfate added. The mixture was stirred at RT for 1 hour and then filtered through celite. The filter cake was washed with further ethyl acetate and the filtrates combined. The solvent was evaporated at reduced pressure and the residue was purified by flash column chromatography eluting with 0-30% ethyl acetate in iso-hexane to afford the title compound (0.854 g, 62%). added filtered through celite The filter cake was washed with further ethyl acetate The solvent was evaporated at reduced pressure the residue was purified by flash column chromatography eluting with 0-30% ethyl acetate in iso-hexane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of methyl 4-(2-methoxyvinyl)benzoate (1.36 g, 7.08 mmol) in methanol (30 mL) was added para-toluenesulfonic acid monohydrate (pTSA) (0.135 g, 0.71 mmol) and the reaction mixture heated under reflux for 18 hours. The solvent was evaporated at reduced pressure. The residue was partitioned between DCM and 10% aqueous potassium carbonate. The organic phase was poured through a hydrophobic frit and the solvent evaporated at reduced pressure. The crude material was used in the next step without further purification. the reaction mixture heated under reflux for 18 hours The solvent was evaporated at reduced pressure The residue was partitioned between DCM and 10% aqueous potassium carbonate The organic phase was poured through a hydrophobic frit the solvent evaporated at reduced pressure The crude material was used in the next step without further purification

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of methyl 4-(2-methoxyvinyl)benzoate (1.36 g, 7.08 mmol) in methanol (30 mL) was added para-toluenesulfonic acid monohydrate (pTSA) (0.135 g, 0.71 mmol) and the reaction mixture heated under reflux for 18 hours. The solvent was evaporated at reduced pressure. The residue was partitioned between DCM and 10% aqueous potassium carbonate. The organic phase was poured through a hydrophobic frit and the solvent evaporated at reduced pressure. The crude material was used in the next step without further purification. the reaction mixture heated under reflux for 18 hours The solvent was evaporated at reduced pressure The residue was partitioned between DCM and 10% aqueous potassium carbonate The organic phase was poured through a hydrophobic frit the solvent evaporated at reduced pressure The crude material was used in the next step without further purification

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of methyl 4-(2-methoxyvinyl)benzoate (1.36 g, 7.08 mmol) in methanol (30 mL) was added para-toluenesulfonic acid monohydrate (pTSA) (0.135 g, 0.71 mmol) and the reaction mixture heated under reflux for 18 hours. The solvent was evaporated at reduced pressure. The residue was partitioned between DCM and 10% aqueous potassium carbonate. The organic phase was poured through a hydrophobic frit and the solvent evaporated at reduced pressure. The crude material was used in the next step without further purification. the reaction mixture heated under reflux for 18 hours The solvent was evaporated at reduced pressure The residue was partitioned between DCM and 10% aqueous potassium carbonate The organic phase was poured through a hydrophobic frit the solvent evaporated at reduced pressure The crude material was used in the next step without further purification

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a cooled (−78° C.) solution of methyl 4-(2,2-dimethoxyethyl)benzoate (assume 7.08 mmol) in THF (30 mL) was added drop wise a solution of lithium aluminium hydride (2.0 M in THF, 3.50 mL, 7.00 mmol). The reaction mixture was allowed to warm to RT over 4 hours. The mixture was sequentially treated with water (0.266 mL), 2M aqueous sodium hydroxide (0.266 mL) and water (3×0.266 mL). The mixture was diluted with ethyl acetate and magnesium sulfate added. The mixture was stirred at RT for 1 hour and then filtered through celite. The filter cake was washed with further ethyl acetate and the filtrates combined. The solvent was evaporated at reduced pressure and the residue was purified by flash column chromatography eluting with 0-30% ethyl acetate in iso-hexane to afford the title compound (0.854 g, 62%). added filtered through celite The filter cake was washed with further ethyl acetate The solvent was evaporated at reduced pressure the residue was purified by flash column chromatography eluting with 0-30% ethyl acetate in iso-hexane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of methyl 4-(2-methoxyvinyl)benzoate (1.36 g, 7.08 mmol) in methanol (30 mL) was added para-toluenesulfonic acid monohydrate (pTSA) (0.135 g, 0.71 mmol) and the reaction mixture heated under reflux for 18 hours. The solvent was evaporated at reduced pressure. The residue was partitioned between DCM and 10% aqueous potassium carbonate. The organic phase was poured through a hydrophobic fit and the solvent evaporated at reduced pressure. The crude material was used in the next step without further purification. the reaction mixture heated under reflux for 18 hours The solvent was evaporated at reduced pressure The residue was partitioned between DCM and 10% aqueous potassium carbonate The organic phase was poured through a hydrophobic fit the solvent evaporated at reduced pressure The crude material was used in the next step without further purification