Sodium borohydride → HCID 86696516, compound

Participants

Reaction Steps

Solid sodium borohydride (110 mg, 2.92 mmol) was added portionwise to a solution of 2-(2-formylcyclopropyl)benzonitrile (500 mg, 2.92 mmol) in methylene chloride (6 mL) and MeOH (10 mL). The mixture was stirred for 2 hr. The reaction was concentrated, and the residue was dissolved in ether and water. The ether layer was separated, washed with water and brine, dried over magnesium sulfate, and concentrated to give 2-(2-(hydroxymethyl)cyclopropyl)benzonitrile as a slightly colored wax (425 mg, 84%). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.63 (dd, J=7.7, 0.9 Hz, 1H), 7.52 (td, J=7.8, 1.0 Hz, 1H), 7.36-7.24 (m, 1H), 7.08 (d, J=8.0 Hz, 1H), 3.87-3.72 (m, 1H), 3.65 (dd, J=11.2, 7.2 Hz, 1H), 2.25-2.13 (m, 1H), 1.82 (br. s., 1H), 1.60 (s, 1H), 1.56-1.45 (m, 1H), 1.12 (ddt, J=15.3, 8.6, 5.3 Hz, 1H). LCMS: M+1=173.1.

Provenance & Evidence