Lithium borohydride → HCID 66801740, compound

Participants

Reaction Conditions

Reaction Steps

To a cooled (0° C.) solution of ethyl 2-(2,6-dichlorophenyl)thiazole-4-carboxylate (7.0 g, 23 mmol) in MeOH (100 mL) was added lithium borohydride (0.98 g, 47 mmol) in four portions. After addition, the mixture was stirred at 0° C. for 1 hour. The reaction mixture was quenched with water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic extract was washed with brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified via silica gel column chromatography eluting with EtOAc/petroleum ether (1:5) to give the desired product as a white solid (6.2 g, 97% yield). 1H NMR (DMSO-d6, 500 MHz): δ 7.74 (s, 1H), 7.66-7.64 (m, 2H), 7.60-7.56 (m, 1H), 5.52 (t, J=5.5 Hz, 1H), 4.70 (m, 2H). LCMS (ESI) m/z: 260.1 [M+H+].

Provenance & Evidence