2,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-pentylpyridine → (+/-)-2,6-Diisopropyl-3-(1-hydroxy-2-butenyl)-4-(4-fluorophenyl)-5-pentylpyridine

Participants

Reaction Steps

The title compound was prepared from 2,6-diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-pentylpyridine (Example 1) and allylmagnesium bromide according to the procedures described in Example 114. 1H NMR (300 MHz, CDCl3): δ 7.09 (m, 4 H), 6.58 (m, 1 H), 5.06 (s, 1 H), 5.01 (m, 1 H), 4.47 (m, 1 H), 3.71 (septet, J=6.6 Hz, 1 H), 3.20 (septet, J=6.6 Hz, 1 H), 2.59 (m, 1 H), 2.35 (m, 1 H), 2.18 (t, J=4.8 Hz, 2 H), 1.72 (d, J=2.9 Hz, 1 H), 1.28 (m, 14 H), 1.11 (m, 4 H), 0.783 (t, J=6.6 Hz, 3 H). FAB-MS: calcd for (C26H36FNO) 397, found 398 (M+H). Anal. Calcd for C26H36FNO: C, 77.88; H, 9.41; N, 3.63; F, 4.93. Found: C, 78.10; H, 9.21; N, 3.43; F, 4.89. mp 70-72° C. Rf=0.2 (50% CH2Cl2/hexane).

Provenance & Evidence