反应详情

To a stirred solution of 1-(5-benzyloxy-2-hydroxyphenyl)ethanone (3.0 g, 12.4 mmol) in anhydrous DMF (15 ml) was added NaH (0.55 g, 13.6 mmol). The mixture was allowed to stir at RT for 30 min and then heated to 60° C. A solution of (R)-oxiran-2-ylmethyl 4-methylbenzenesulfonate (2.83 g, 12.4 mmol) in DMF was added dropwise at 60° C. during 1 h. Stirring was then continued at 60° C. for 3 h. The cooled 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/toluene as eluent to afford the title compound (2.35 g) as a white solid.

1. temperatureheated to 60° C
2. stirringStirring
3. waitwas then continued at 60° C. for 3 h
4. customThe cooled reaction
5. customwas quenched by addition of water (80 ml)
6. extractionextracted three times with EtOAc
7. extractionThe combined organic layers were extracted twice with aq 1 M NaOH
8. washwashed with water and brine
9. dry with materialThe organic layer was dried with Na2SO4
10. concentrationconcentrated
11. customThe crude product obtained
12. customwas purified by column chromatography with EtOAc/toluene as eluent