反应详情

To a stirred solution of 1-(4-(benzyloxy)-2-hydroxyphenyl)ethanone (3.36 g, 13.9 mmol) in anhydrous DMF (15 ml) was added NaH (0.62 g, 15.5 mmol). The mixture was allowed to stir at RT for 30 min, and a solution of (R)-oxiran-2-ylmethyl 4-methylbenzenesulfonate (3.17 g, 13.9 mmol) in DMF was added dropwise at RT. The mixture was slowly heated to 60° C. and stirred for 3 h. The reaction was quenched by addition of water (80 ml) and extracted three times with EtOAc. The combined organic layers were extracted twice with aq 1 M NaOH and washed with water and brine. The organic layer was dried with Na2SO4 and concentrated. The crude product obtained was purified by column chromatography with EtOAc/heptane (1:1) as eluent to afford the title compound (2.64 g) as a white solid.

1. temperatureThe mixture was slowly heated to 60° C.
2. stirringstirred for 3 h
3. customThe reaction was quenched by addition of water (80 ml)
4. extractionextracted three times with EtOAc
5. extractionThe combined organic layers were extracted twice with aq 1 M NaOH
6. washwashed with water and brine
7. dry with materialThe organic layer was dried with Na2SO4
8. concentrationconcentrated
9. customThe crude product obtained
10. customwas purified by column chromatography with EtOAc/heptane (1:1) as eluent