2-(4-Chlorophenyl)-1,3-thiazole-5-carbaldehyde → 1-[2-(4-Chlorophenyl)thiazol-5-yl]ethanol

To a solution of 2-(4-Chloro-phenyl)-thiazole-5-carbaldehyde (4.95 g, 22.14 mmol) in THF (65 ml) at 0° C. under an atmosphere of nitrogen was added methyl magnesium chloride (3M in THF; 8.11 ml, 24.35 mmol) dropwise over a period of 5 minutes. The reaction was then allowed to warm to room temperature and stirred for a further 2 hours. The reaction was quenched with saturated aqueous ammonium chloride solution (100 ml) and stirred for 5 minutes, before the methanol is 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 1-[2-(4-Chloro-phenyl)-thiazol-5-yl]-ethanol (4.71 g).

1. customThe reaction was quenched with saturated aqueous ammonium chloride solution (100 ml)
2. stirringstirred for 5 minutes, before the methanol
3. customis 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-8e375aa1ec0848efa881966e3c6c591d

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09051300B2