Ethyl acetate hexane → 1-[4-(4-Fluoro-phenyl)-5-hexyl-2,6-diisopropyl-pyridin-3-yl]-ethanol

HRID 324830Notes

Reaction equation

HRID 324830 reaction equation
[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:7]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:6]([CH:25]([CH3:27])[CH3:26])[N:5]=1)([CH3:3])[CH3:2].[C:28](OCC)(=O)C.CCCCCC>>[CH:1]([C:4]1[C:9]([CH:10]([OH:11])[CH3:28])=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[C:7]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:6]([CH:25]([CH3:26])[CH3:27])[N:5]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 220050152,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-hexylpyridine

Product 1

HCID 220049881-[4-(4-Fluoro-phenyl)-5-hexyl-2,6-diisopropyl-pyridin-3-yl]-ethanol

Procedure

The title compound was prepared from 2,6-diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-hexylpyridine (Example 23) according to the procedures described in Example 101. 1H NMR (300 MHz, CDCl3): δ 7.13 (m, 3 H), 7.04 (m, 1 H), 4.65 (m, 1 H), 3.73 (sept, J=6.6 Hz, 1 H), 3.19 (sept, J=6.6 Hz, 1 H), 2.18 (m, 2 H), 1.39 (d, J=6.6 Hz, 3 H), 1.30 (m, 13 H), 1.18 (m, 4 H), 1.09 (m, 4 H), 0.81 (t, J=7 Hz, 3 H). FAB-MS: calcd for (C25H36FNO) 385, found 386 (M+H). Anal. Calcd for C25H36FNO: C, 77.88; H, 9.41; N, 3.63. Found: C, 77.84; H, 9.49; N, 3.65. mp 96-99° C. Rf=0.3 (10% ethyl acetate/hexane).

Sources & evidence

ORD record
ord-b7997cd7d568419db182c9e4a9536a1e
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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