Water → 3-[p-(3-Hydroxy-2-methyl-1-propenyl)benzyl]pyridine

反応式

Cl[CH:2]([C:7]1[CH:19]=[CH:18][C:10]([CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:9][CH:8]=1)[CH:3]([CH3:6])[CH2:4][OH:5].C1CCN2C(=NCCC2)CC1.O>CN(C)C=O>[OH:5][CH2:4][C:3]([CH3:6])=[CH:2][C:7]1[CH:19]=[CH:18][C:10]([CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:9][CH:8]=1

参加物

実験手順

In 1.3 ml of N,N-dimethylformamide was dissolved 260 mg of 3-[p-(1-chloro-3-hydroxy-2-methylpropyl)benzyl]pyridine, and 0.28 ml of DBU was added to the resulting solution after which the resulting mixture was subjected to reaction at a temperature of 110° to 120° C. for one hour. To the reaction mixture was added 5 ml of water, and the mixture was subjected to extraction with two 5-ml portions of ethyl acetate. The extracts were combined, washed with 3 ml of water, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a colomn chromatography [Wako Silica Gel C-200, eluant: benzene:ethyl acetate (3:1 by volume)] to obtain 150 mg (yield 62.7%) of colorless, oily 3-[p-(3-hydroxy-2-methyl-1-propenyl)benzyl]pyridine.