[Br-].[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:5][CH:4]=1.C([Li])CCC.[N+:35]([C:38]1[CH:45]=[CH:44][C:41]([CH:42]=O)=[CH:40][CH:39]=1)([O-:37])=[O:36]>O1CCCC1.CCCCCC.O>[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH:10]=[CH:42][C:41]2[CH:44]=[CH:45][C:38]([N+:35]([O-:37])=[O:36])=[CH:39][CH:40]=2)=[CH:7][CH:8]=1
To a suspension of [2-(4-methylphenyl)ethyl]triphenyl-phosphonium bromide (55.4 g) in anhydrous tetrahydrofuran (840 ml) kept at -50° C., a 1.5 N solution of n-butyl lithium in hexane (80 ml) was added, and the resultant mixture was stirred for a while. A solution of p-nitrobenzaldehyde (15.1 g) in anhydrous tetrahydrofuran (100 ml) was added thereto. The resulting mixture was allowed to stand at room temperature overnight, diluted with water and extracted with ethyl acetate. The extract was concentrated under reduced pressure and chromatographed on a column with silica gel, followed by eluting with a mixture of hexane and ethyl acetate to give 4-[3-(4-methylphenyl)-1-propenyl]nitrobenzene (21 g). nD24 1.5321.
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