Benzaldehyde → 2,6-Diethyl-3-hydroxymethyl4-phenyl-5-(1-ethenyl)pyridine

Participants

Reaction Steps

The title compound was prepared from ethyl propionylacetate, benzaldehyde and methyl triphenylphosphonium bromide/sodium amide according to the procedures descnbed in Example 1, Steps A-G. 1H NMR (300 MHz, CDCl3): δ7.40 (m, 3 H), 7.20 (m, 2 H), 6.36 (dd, J=11, 18 Hz, 1 H), 5.22 (dd, J=11, 2Hz, 1 H), 5.00 (dd, J=18, 2 Hz, 1 H), 4.41 (d, J=6 Hz, 2 H), 2.96 (m, 4 H), 1.35 (m, 7 H). FAB-MS: calculated for (C18H21NO) 267, found 268 (M+H). Anal. Calcd for C18H21NO: C, 80.86; H, 7.92; N, 5.24. Found: C, 80.65; H, 8.06; N, 5.09. mp 84-85° C. Rf=0.4 (50% ethyl acetate/hexane).

Provenance & Evidence