Water → 2-Bromo-1-(1,3-thiazol-5-yl)ethan-1-ol

Reaction equation

[BH4-].[Na+].[Br:3][CH2:4][C:5]([C:7]1[S:11][CH:10]=[N:9][CH:8]=1)=[O:6].O>CO>[Br:3][CH2:4][CH:5]([C:7]1[S:11][CH:10]=[N:9][CH:8]=1)[OH:6]

Participants

Procedure

Sodium borohydride (38 mg, 1.0 mmol) was added in one portion to a solution of 207 mg (1.0 mmol) of the product from Example 3 in 2 mL of methanol at 0° C. After stirring for 0.75 h, water was added and the mixture extracted three times with diethyl ether. The combined organic phase was washed with brine, dried(MgSO4) and the solvent removed in vacuo. Flash chromatography (silica gel, 30-40% ethyl acetate-hexanes) afforded 130 mg (62%) of the title compound as a colorless oil: 1H NMR (400 MHz, CDCl3) δ8.78 (s, 1H), 7.83 (s, 1H), 5.28-5.24 (m, 1H), 3.70 (dd, 1H, J=10.6, 3.9 Hz), 3.61 (dd, 1H, J=10.6, 7.9 Hz), 2.95 (d, 1H, J=4.3 Hz).