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

HRID 324809Notes

Reaction equation

HRID 324809 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-].[CH2:22]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[NH2-:48].[Na+]>C(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:6](/[CH:7]=[CH:22]/[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[C:1]([CH:2]([CH3:4])[CH3:3])[N:48]=1)([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 680234-FluorobenzaldehydeHCID 81583Ethyl isobutyrylacetateHCID 16211268Sodium;azanide;benzyl(triphenyl)phosphanium;bromide

Product 1

HCID 220049932,6-Diisopropyl-3hydroxymethyl-4-(4-fluorophenyl)-5-[2(E)-phenyl-ethenyl]pyridine

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

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).

Sources & evidence

ORD record
ord-491611503c5546a2bd354673249d863c
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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