Diethyl P-((4-methylphenyl)methyl)phosphonate → 2-(4-Methylphenyl)-1-(5-phenylthien-2-yl)ethene

反応式

[CH:1]([C:3]1[S:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)=O.[CH3:14][C:15]1[CH:29]=[CH:28][C:18]([CH2:19]P(=O)(OCC)OCC)=[CH:17][CH:16]=1.C[O-].[Na+]>CN(C)C=O>[CH3:14][C:15]1[CH:29]=[CH:28][C:18]([CH:19]=[CH:1][C:3]2[S:4][C:5]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)=[CH:17][CH:16]=1

参加物

実験手順

To a stirred solution of 1.52 gram (0.008 mole) of 2-formyl-5-phenylthiophene and 2.0 grams (0.00820 mole) of diethyl 4-methylbenzylphosphonate in 40 mL of N,N-dimethylformamide was added 0.53 gram (0.0098 mole) of sodium methoxide. The reaction mixture was stirred at room temperature for approximately 18 hours and then was quenched with 50 mL of an aqueous solution saturated with ammonium chloride. A precipitate formed and was collected by filtration. The filter cake was washed with water. The washed solid was purified by column chromatography on silica gel, eluting with chloroform:n-hexane (10:90) yielded 1.1 gram of 2-(4-methylphenyl)-1-(5-phenylthien-2-yl)ethene as a solid, m.p. 159°-160° C.