4-Fluorobenzaldehyde → [4-(4-Fluoro-phenyl)-2,6-diisopropyl-5-vinyl-pyridin-3-yl]-methanol
Reaction equation
[C:1]([CH2:6][C:7]([O:9]CC)=O)(=O)[CH:2]([CH3:4])[CH3:3].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.[Br-].C[P+]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(C1C=CC=CC=1)C1C=CC=CC=1.[NH2-:42].[Na+].[C:44](OCC)(=O)C.CCCCCC>>[CH:2]([C:1]1[C:6]([CH2:7][OH:9])=[C:17]([C:16]2[CH:19]=[CH:20][C:13]([F:12])=[CH:14][CH:15]=2)[C:40]([CH:41]=[CH2:36])=[C:39]([CH:38]([CH3:37])[CH3:44])[N:42]=1)([CH3:3])[CH3:4]Participants
5
Procedure
The title compound was prepared from ethyl isobutyrylacetate, 4-fluorobenzaldehyde and methyl triphenylphosphonium bromide/sodium amide according to the procedures described in Example 1, Steps A-G. 1H NMR (300 MHz, CDCl3): δ7.12 (m, 4 H), 6.35 (dd, J=11.5,18 Hz, 1 H), 5.24 (dd, J=1.5, 11.4 Hz, 1 H), 4.97 (dd, J=1.5, 18 Hz, 1 H), 4.41 (d, J=5.5 Hz, 2 H), 3.44 (sept, J=6.6 Hz, 2 H), 1.35 (d, J=6.6 Hz, 6 H), 1.28 (d, J=6.6 Hz, 6 H), 1.25 (m, 1 H). FAB-MS: calculated for (C20OH24FNO) 313, found 314 (M+H). Anal. Calcd for C2OH24FNO: C, 76.65; H, 7.72; N, 4.47. Found: C, 76.87; H, 7.79; N, 4.33. mp 119-120° C. Rf=0.4 (20% ethyl acetate/hexane).
Sources & evidence
- ORD record
- ord-dfdbe10671ae4f2b983e0a5d181df436
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06218431B1
Reaction notes
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