Sodium borohydride → HCID 28945889, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 3-(4-formyl-phenoxy)-benzonitrile of Preparation 10 (0.90 g, 4.04 mmol) in methanol (15 mL) and cool to 0° C. Add sodium borohydride (0.31 g, 8.08 mmol) in three batches. After 1 hr, allow to warm to ambient temperature and stir overnight. Concentrate under reduced pressure to give a residue. Dilute with ethyl acetate (50 mL) and wash with 1N hydrochloric acid (3×100 mL). Separate layers and dry the organic layer over magnesium sulfate, filter, and concentrate to a residue. Purification by flash chromatography, using 10% ethyl acetate/hexanes to 50% ethyl acetate/hexanes as a gradient eluent gives the title product (0.83 g, 91%): 1H NMR δ (CDCl3) 7.48-7.38 (m, 4H), 7.30-7.23 (m, 2H), 7.06 (d, J=8.4 Hz, 2H), 4.75 (s, 2H).

Provenance & Evidence