Water → 4-(2-Hydroxyethyl)-2-methoxybenzonitrile

Participants

Reaction Steps

LiBH4 (1.7 mL, 3.4 mmol, 2 M in THF) was added to a stirred solution of ethyl(4-cyano-3-methoxyphenyl)acetate (0.50 g, 2.4 mmol) in THF (25 mL) at 0° C. The resulting solution was stirred for 12 h. Water (15 ml) was added, and the resulting solution was extracted with dichloromethane (2×50 ml). The combined organic layers were dried over MgSO4, filtered, and evaporated under reduced pressure. The residue was purified by column chromatography eluting with EtOAc-Hexanes (7:3→1:1) to give 4-(2-hydroxyethyl)-2-methoxybenzonitrile. 1H NMR (500 MHz, CDCl3) δ 7.52 (d, 1H, J=7.0 Hz), 6.91 (d, 1H, J=7.8 Hz), 6.88 (s, 1H), 3.95 (s, 3H), 3.92 (t, 2H, J=6.4 Hz), 2.93 (t, 2H, J=6.4 Hz); LCMS: [(M+1)]+=178.3; tR=2.1 min.

Provenance & Evidence