Sodium borohydride → HCID 86680634, compound

Participants

Reaction Steps

To a solution of 5-(5-acetylthiophen-2-yl)-1-methylpyridin-2(1H)-one (0.65 g, 2.78 mmol) in THF (8 mL) and MeOH (8 mL) was added NaBH4 (0.26 g, 6.97 mmol) under nitrogen. The mixture was stirred at rt for 10 min, quenched with ammonium chloride solution (15 mL) and extracted with ethyl acetate (2×100 mL). The organic extracts were washed with brine solution (2×50 mL), dried over sodium sulphate and evaporated to obtain the crude compound. Purification by flash chromatography (100-200μ; 100% ethyl acetate) afforded 5-(5-(1-hydroxyethyl)thiophen-2-yl)-1-methylpyridin-2(1H)-one (0.5 g, 76% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.00 (s, 1H), 7.69 (d, 1H), 7.07 (d, 1H), 6.83 (d, 1H), 6.43 (d, 1H), 5.51 (bs, 1H), 4.88 (q, 1H), 3.45 (s, 3H), 1.38 (d, 3H); LC-MS m/z calcd for [M+H]+ 236.07 found 236.3.

Provenance & Evidence