4-Fluorobenzaldehyde → 2,6-Diisopropyl-3hydroxymethyl-4-(4-fluorophenyl)-5-[2(E)-phenyl-ethenyl]pyridine

Participants

Reaction Steps

The title compound was prepared from ethyl isobutyrylacetate, 4-fluorobenzaldehyde and benzyl triphenylphosphonium bromide/sodium amide according to the procedures described in Example 1, Steps A-G. 1H NMR (300 MHz, CDCl3): δ7.21 (m, 9 H), 6.70 (d, J=16.5 Hz, 1 H), 6.26 (d, J=16.5 Hz, 1 H), 4.45 (d, J=5.5 Hz, 2 H), 3.48 (sept, J=6.6 Hz, 2 H), 1.37 (d, J=6.6 Hz, 6 H), 1.31 (d, J =6.6 Hz, 6 H), 1.29 (m, 1 H). FAB-MS: calculated for (C26H28FNO) 389, found 390 (M+H). Anal. Calcd for C26H28FNO: C, 80.17; H, 7.25; N, 3.60. Found: C, 79.89; H, 7.28; N, 3.49. mp 107-110° C. Rf=0.3 (20% ethyl acetate/hexane).

Provenance & Evidence