Potassium Hydroxide → (4-Phenyl-1,3-thiazol-2-yl)methanol

Participants

Reaction Steps

Potassium hydroxide (1.06 g, 18.84 mmol) was added to an ice cooled solution of benzoic acid (4-phenylthiazol-2-yl)methyl benzoate (3.71 g, 12.56 mmol) in EtOH (40 mL). The reaction mixture was slowly warmed to room temperature and allowed to stir for 1 h. The reaction mixture was concentrated under reduced pressure and then diluted with water. The organic product was extracted with EtOAc, washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by column chromatography (silica 60-120 mesh, eluant 10% EtOAc in petroleum ether) to get the pure (4-phenylthiazol-2-yl)methanol (2.1 g, yield 87%). 1H NMR (400 MHz, CDCl3) δ 7.89-7.87 (m, 2H), 7.46-7.41 (m, 3H), 7.37-7.33 (m, 1H), 5.01 (s, 2H). MS (ESI) m/z: Calculated for C10H9NOS: 191.04. found: 192.2 (M+H)+.

Provenance & Evidence