Propylene Oxide → 3-((s)-2-Hydroxypropylthio)phenylboronic acid
Reaction equation
[CH2:1]1[O:4][CH:2]1[CH3:3].[SH:5][C:6]1[CH:7]=[C:8]([B:12]([OH:14])[OH:13])[CH:9]=[CH:10][CH:11]=1.[O-2].[Al+3].[O-2].[O-2].[Al+3]>C(OCC)C>[OH:4][C@@H:2]([CH3:3])[CH2:1][S:5][C:6]1[CH:7]=[C:8]([B:12]([OH:14])[OH:13])[CH:9]=[CH:10][CH:11]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.