Sodium borohydride → HCID 70975527, compound

Participants

Reaction Steps

Sodium borohydride (36 mg, 0.96 mmol) was added to a solution of compound 1 (300 mg, 0.96 mmol) in ethanol at 0° C., in portions. The reaction mixture was stirred at room temperature for 1 h. The solvent was evaporated to dryness. The residue was dissolved in chloroform, and the organic phase was washed with brine and water. The organic layer was dried over sodium sulfate, and concentrated to dryness. The crude product was passed through silica column, and eluted with 70% ethyl acetate in hexanes. The title compound 10 was obtained as colorless thick syrup (296 mg, 98% yield). Rf (60:40 ethyl acetate:hexanes)=0.10. 1H NMR (300 MHz, CDCl3): δ 7.25 (s, 1H), 7.00 (q, 2H, Ar—H, J=7.4), 6.93 (t, 2H, Ar—H, J=7.8), 6.86 (t, 2H, Ar—H, J=7.0), 6.81 (t, 2H, Ar—H, J=7.6), 6.39 (s, 2H, C═CH), 4.66 (s, 1H), 3.61 (d, 2H, J=14.8), 3.25 (d, 2H, J=14.8). 13C NMR (75 MHz, CDCl3): δ 161.42 (d, J=246.2), 144.36, 130.74, 128.50, 128.60, 128.49, 124.31, 124.12, 123.64, 115.43, 115.14, 75.62, 45.68. ESI Mass calculated for C19H17F2NO (M)+313.13. found 313.87.

Provenance & Evidence