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