Benzaldehyde → 2,6-Diethyl-3-hydroxymethyl4-phenyl-5-(1-ethenyl)pyridine

HRID 324799Notes

Reaction equation

HRID 324799 reaction equation
[C:1]([CH2:5][C:6]([O:8]CC)=O)(=O)[CH2:2][CH3:3].[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[NH2-:40].[Na+]>C(OCC)(=O)C.CCCCCC>[CH2:2]([C:1]1[C:5]([CH2:6][OH:8])=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:23]([CH:24]=[CH2:25])=[C:22]([CH2:27][CH3:26])[N:40]=1)[CH3:3]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 78656Ethyl 3-oxovalerateHCID 16212304Sodium;azanide;methyl(triphenyl)phosphanium;bromide

Product 1

HCID 220049462,6-Diethyl-3-hydroxymethyl4-phenyl-5-(1-ethenyl)pyridine

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The title compound was prepared from ethyl propionylacetate, benzaldehyde and methyl triphenylphosphonium bromide/sodium amide according to the procedures descnbed in Example 1, Steps A-G. 1H NMR (300 MHz, CDCl3): δ7.40 (m, 3 H), 7.20 (m, 2 H), 6.36 (dd, J=11, 18 Hz, 1 H), 5.22 (dd, J=11, 2Hz, 1 H), 5.00 (dd, J=18, 2 Hz, 1 H), 4.41 (d, J=6 Hz, 2 H), 2.96 (m, 4 H), 1.35 (m, 7 H). FAB-MS: calculated for (C18H21NO) 267, found 268 (M+H). Anal. Calcd for C18H21NO: C, 80.86; H, 7.92; N, 5.24. Found: C, 80.65; H, 8.06; N, 5.09. mp 84-85° C. Rf=0.4 (50% ethyl acetate/hexane).

Sources & evidence

ORD record
ord-c0e5860b50444694bc626b77388cad4f
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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