Diethyl Ether → 5-(5-(1-hydroxyethyl)thiophen-2-yl)-1-isopropylpyridin-2(1H)-one

Participants

Reaction Steps

A solution of 5-(1-isopropyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-carbaldehyde (0.205 g, 0.829 mmol) in THF (10 mL) was cooled to 0° C. A solution of 1.5M methyl magnesium bromide in diethyl ether (1.65 mL, 2.48 mmol) was added slowly at 0° C. and the mixture was stirred for 2 h at rt. The reaction mixture was quenched with saturated NH4Cl solution (10 mL) and extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution (10 mL), dried over Na2SO4 and concentrated under vacuum to obtain crude 5-(5-(1-hydroxyethyl)thiophen-2-yl)-1-isopropylpyridin-2(1H)-one as an off-white solid (0.150 g, 71% yield). LC-MS m/z calcd for [M+H]+ 264.1. found 264.1.

Provenance & Evidence