反应详情

10 ml (20 mmole) 2 M borane dimethyl sulfide complex in diethyl ether was slowly added to 6.3 g (18.1 mmole) 2,4-dibenzyloxyphenyl acetic acid dissolved in 50 ml dry tetrahydrofuran cooled on an ice bath under nitrogen and then stirred for 7 days at room temperature. The reaction was quenched with water and extracted with ethyl acetate, dried with magnesium sulfate and evaporated. The crude product was purified by chromatography on silica gel using dichloromethane/methanol as eluent to give 2.63 g of the desired product and a mixture of 2,4-dibenzyloxyphenyl acetic acid and the desired product. The mixture was dissolved in 100 ml ethyl acetate, 0.152 g (4 mmole) lithium aluminum hydride was added in portions and the mixture was stirred at room temperature for 6 hours. After 4 hours some more lithium aluminum hydride was added. The reaction was quenched with 1% hydrochloric acid and the solution was filtered. The filtrate was dried with magnesium sulfate and evaporated in vacuo to give 1.3 g more of 2-[2,4-di(benzyloxy)phenyl]-1-ethanol (total yield 3.9 g, 64.4%).

1. temperaturecooled on an ice bath under nitrogen
2. customThe reaction was quenched with water
3. extractionextracted with ethyl acetate
4. dry with materialdried with magnesium sulfate
5. customevaporated
6. customThe crude product was purified by chromatography on silica gel