Benzaldehyde → trans-2-Methyl-4-styryl-pyridine 1-oxide

HRID 1797100Notes

Reaction equation

HRID 1797100 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N+:3]=1[O-:9].C([O-])(C)(C)C.[K+].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH3:1][C:2]1[CH:7]=[C:6](/[CH:8]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[CH:4][N+:3]=1[O-:9]

Participants

4

Reactant 3

HCID 240BenzaldehydeHCID 707332,4-Dimethylpyridine 1-oxideHCID 23665647Potassium tert-butoxide

Product 1

HCID 22176472trans-2-Methyl-4-styryl-pyridine 1-oxideYield 7%

Procedure

Following the general method described in example 2a, 2,4-dimethylpyridine 1-oxide was reacted with potassium tert.-butanolate and benzaldehyde. After extraction and chromatography (SiO2 with CH2Cl2/MeOH=97/3) the title compound was obtained as a yellow solid material (yield 7%). NMR (250 MHz, DMSO): 2.37 (s, 3H, CH3), 7.20 (d, J=16.5 Hz, 1H, CH═CH), 7.25–7.75 (m, 8H, arom-H, CH═CH), 8.22 (d, J=6.8 Hz, 1H, arom-H).

Workup

  1. extractionAfter extraction and chromatography (SiO2 with CH2Cl2/MeOH=97/3) the title compound

Sources & evidence

ORD record
ord-7506ef6cbfb246e3baf7507cfe8536f5
Source dataset
uspto-grants-2006_04
Patent number
US07034044B2

Reaction notes

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