6-Phenylnicotinaldehyde → 1-(6-Phenylpyridin-3-yl)propan-1-ol

Participants

Reaction Steps

Synthesized using compound 43b (313 mg, 1.71 mmol) and ethylmagnesium bromide (3.42 mL, 3.42 mmol, 1 M in THF) according to Method D. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (3:1) as eluent. Light yellow solid. Yield: 298 mg, 82%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=0.90-0.95 (m, 3H) 1.71-1.88 (m, 2H) 4.62 (t, J=6.62 Hz, 1H) 7.38-7.43 (m, 1H) 7.43-7.49 (m, 2H) 7.64-7.67 (m, 1H) 7.69-7.73 (m, 1H) 7.92-7.96 (m, 2H) 8.54 (d, J=2.21 Hz, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=9.9, 31.7, 73.2, 120.3, 126.8, 128.7, 128.8, 134.5, 138.3, 139.0, 147.7, 156.5; MS (ESI): m/z=214.28 [M+H]+.

Provenance & Evidence