[4-(4-Fluoro-phenyl)-2,6-diisopropyl-5-vinyl-pyridin-3-yl]-methanol → [5-Ethyl-4-(4-fluoro-phenyl)-2,6-diisopropyl-pyridin-3-yl]-methanol

HRID 324806Notes

Reaction equation

HRID 324806 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]([CH:19]=[CH2:20])=[C:6]([CH:21]([CH3:23])[CH3:22])[N:5]=1)([CH3:3])[CH3:2]>C(OCC)(=O)C.CCCCCC>[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[C:7]([CH2:19][CH3:20])=[C:6]([CH:21]([CH3:22])[CH3:23])[N:5]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 22004897[4-(4-Fluoro-phenyl)-2,6-diisopropyl-5-vinyl-pyridin-3-yl]-methanol

Product 1

HCID 22004918[5-Ethyl-4-(4-fluoro-phenyl)-2,6-diisopropyl-pyridin-3-yl]-methanol

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound was prepared from 2,6dusopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5ethenylpyridine (Example 22) according to the procedure described in Example 1, Step H. 1H NMR (300 MHz, CDCl3): δ7.15 (m, 4 H), 4.33 (d, J=3.6 Hz, 2 H), 3.41 (sept, J=6.6 Hz, 1 H), 3.26 (sept, J=6.6 Hz, 1 H), 2.34 (q, J=7.35 Hz, 2 H), 1.33 (d, J=6.6 Hz, 6 H), 1.31 (d, J=6.6 Hz, 6 H), 1.19 (m, 1 H), 0.93 (t, J=7.35 Hz, 3 H). FAB-MS: calculated for (C20H26FNO) 315, found 316 (M+H). Anal. Caled for C20H26FNO: C, 76.16; H, 8.31; N, 4.44. Found: C, 75.74; H, 8.50; N, 4.27. mp 126-129° C. Rf=0.4 (20% ethyl acetate/hexane).

Sources & evidence

ORD record
ord-6686d26dc06d4eae9d3e731c384be175
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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