2-Vinylpyridine → 2-(2,4-Dimethylcyclohex-3-en-1-yl)pyridine

HRID 131087Notes

Reaction equation

HRID 131087 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][CH2:4][CH:3]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.C(C1C=CC=CN=1)=C.CC(C=CC)=C>N1C=CC=CC=1>[CH3:1][CH:2]1[CH:7]=[C:6]([CH3:8])[CH2:5][CH2:4][CH:3]1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 75212-VinylpyridineHCID 142381,3-Pentadiene, 2-methyl-HCID 17972404Pyridine, 2-(2,4-dimethylcyclohexyl)-

Product 1

HCID 179724032-(2,4-Dimethylcyclohex-3-en-1-yl)pyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The pyridine of the invention, that is 2-(2,4-dimethylcyclohexyl)pyridine, may be synthesised by a Diels-Alder reaction between 2-vinylpyridine and 2-methyl-1,3-pentadiene to produce 2-(2,4-dimethylcyclohex-3-en-1-yl)pyridine, which is then subjected to a hydrogenation reaction to give 2-(2,4-dimethylcyclohexyl)pyridine. The reaction may be shown schematically as follows:

Sources & evidence

ORD record
ord-c912a90d851b4179a43a02879338170f
Source dataset
uspto-grants-2008_06
Patent number
US07384905B2

Reaction notes

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