Sodium borohydride → HCID 119086991, compound

Participants

Reaction Steps

To a solution of ethyl (2E)-3-(3-bromophenyl)prop-2-enoate and ethyl (2Z)-3-(5-bromopyridin-3-yl)prop-2-enoate (4:1 ratio of isomers, 332 mg, 1.30 mmol) in methanol (10 mL) and water (2.5 mL) was added copper (I) chloride (257 mg, 2.59 mmol) and sodium borohydride (98 mg, 2.59 mmol). After 15 minutes, the reaction was diluted with ethyl acetate and filtered through CELITE. The filtrate was washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography to afford ethyl 3-(5-bromopyridin-3-yl)propanoate. MS ESI calc'd. for C10H13BrNO2 [M+H]+ 258 and 260. found 258 and 260. 1H NMR (500 MHz, DMSO-d6) δ 8.52 (d, J=2.2 Hz, 1H), 8.44 (d, J=1.8 Hz, 1H), 7.96 (t, J=2.0 Hz, 1H), 4.02 (q, J=7.1 Hz, 2H), 2.84 (t, J=7.5 Hz, 2H), 2.67 (t, J=7.5 Hz, 2H), 1.12 (t, J=7.1 Hz, 3H).

Provenance & Evidence