Sodium borohydride → 4-[2-(2-Hydroxyethyl)-2,3-dihydro-1-benzofuran-5-yl]benzonitrile

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Reaction Steps

A solution of Example 67B (0.25 g, 0.95 mmol) and sodium borohydride (0.054 g, 1.42 mmol)in methanol (5 mL) was stirred for 1 hour, cooled on ice and quenched with aqueous NaHCO3 (50 mL). The mixture was extracted with dichloromethane (3×100 mL), the organic extracts combined and washed with water (1×150 mL), brine (1×150 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to provide the titled compound (0.24 g, 95%). 1HNMR (CDCl3): 1.90 (m, 2H), 2.90 (m, 2H), 3.46 (m, 2H), 5.40 (m, 1H), 6.85 (d, J=7 Hz, 1H), 7.38 (m, 2H), 7.65 (m, 4H); MS (DCI) 265 (M+), 283 (M+NH4+).

Provenance & Evidence