Sodium borohydride → 3-(4-Phenylthiazol-2-yl)propan-1-ol
Reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][CH2:13][C:14](OCC)=[O:15])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>CO.O>[C:1]1([C:7]2[N:8]=[C:9]([CH2:12][CH2:13][CH2:14][OH:15])[S:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of ethyl 3-(4-phenylthiazol-2-yl)propanoate (0.5 g, 1.91 mmol) in MeOH—H2O (10 mL, 9:1 v/v) was cooled to 0° C. and sodium borohydride (0.29 g, 7.65 mmol) was added. The reaction mixture was warmed to room temperature and further stirred for 8 h. The mixture was quenched with ice water and the organic product was extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure to afford 3-(4-phenylthiazol-2-yl)propan-1-ol (0.4 g, yield 95%) as colorless liquid, which was carried through without further purification. 1H NMR (400 MHz, CDCl3) δ 7.87-7.85 (m, 2H), 7.44-7.40 (m, 2H), 7.35-7.32 (m, 2H), 3.83-3.81 (t, J=5.8 Hz, 2H), 3.24-3.21 (m, 3H), 2.14-2.08 (m, 2H). MS (ESI) m/z: Calculated for C12H13NOS: 219.07. found: 220.2 (M+H)+.