反应详情

S-(−) Propylene oxide (152 μL) was added to a mixture of 500 mg of 3-mercaptophenylboronic acid and aluminum oxide (˜30 eq, neutral, activated, ˜150 mesh) in diethyl ether at room temperature. The reaction was monitored by LC/MS until complete. The reaction mixture was evaporated, and then added 1N HCl. The resulting mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over MgSO4, filtered and evaporated to give 3-((S)-2-hydroxypropylthio)phenylboronic acid (414 mg, 90%). The crude product was directly used for next step reaction without purification.

1. customThe reaction mixture was evaporated
2. additionadded 1N HCl
3. extractionThe resulting mixture was extracted with ethyl acetate (3×50 mL)
4. dry with materialThe combined organic layers were dried over MgSO4
5. filtrationfiltered
6. customevaporated