Sodium borohydride → HCID 10198426, compound

Participants

Reaction Steps

A suspension of (E)-2-(4,6-difluoro-3-oxo-1-indanylidene)acetamide (0.100 g, 0.45 mmol) and sodium borohydride (0.017 g, 0.45 mmol) in 95% ethanol was stirred at ambient temperature for 2 hours. The mixture was cooled in an ice bath and quenched with 0.1N hydrochloric acid (3 mL). The ethanol was evaporated in vacuo, and the residue was dissolved in ethyl acetate (50 mL), washed successively with water (2×30 mL) and brine (30 mL), dried over sodium sulfate, filtered, and evaporated in vacuo. The resudue was washed successively with cold ethyl acetate, hexane, and diethyl ether to give 0.046 g (45%) of (E)-2-(4,6-difluoro-3-hydroxy-1-indanylidene)acetamide as a white solid; mp 232-237° C. (dec.) 1H-NMR (DMSO-d6): δ7.06-7.42 (m, 4H), 6.49 (s, 1H), 5.52 (d, 1H), 5.30 (m, 1H), 3.44 (m, 1H), 3.03 (d, 1H).

Provenance & Evidence