Sodium borohydride → [2-(4-Chlorophenyl)thiazol-5-yl]methanol

To a solution of 2-(4-Chloro-phenyl)-thiazole-5-carbaldehyde (5.59 g, 25 mmol) in methanol (65 ml) at 0° C. was added sodium borohydride (1.04 g, 27.5 mmol) portionwise over a period of 5 minutes. The reaction was then allowed to warm to room temperature and stirred under nitrogen for 3 hours. The reaction was quenched with saturated aqueous ammonium chloride solution (100 ml) and stirred for 5 minutes, before the methanol was removed under reduced pressure. The resulting heterogeneous mixture was then extracted with ethyl acetate (2×100 ml), the combined organics dried over magnesium sulphate and the solvent removed under reduced pressure to give [2-(4-Chloro-phenyl)-thiazol-5-yl]-methanol (5.27 g).

1. customThe reaction was quenched with saturated aqueous ammonium chloride solution (100 ml)
2. stirringstirred for 5 minutes, before the methanol
3. customwas removed under reduced pressure
4. extractionThe resulting heterogeneous mixture was then extracted with ethyl acetate (2×100 ml)
5. dry with materialthe combined organics dried over magnesium sulphate
6. customthe solvent removed under reduced pressure

ORD record

ord-8148b20e0d3248ca8ec18c1de5b79709

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09051300B2