(1,1'-Biphenyl)-4-carboxaldehyde → 1,1'-Biphenyl, ethenyl-

反応式

[CH3:1][C:2](C)([O-])C.[K+].[C:7]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][C:10](C=O)=[CH:9][CH:8]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH:1]([C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[CH2:2]

参加物

実験手順

To a suspension of methyltriphenylphosphonium bromide (5.10 g, 14.27 mmol) in THF (26 mL) was slowly added potassium tert-butoxide (1M solution in THF, 14.27 mL) over ˜20 min at 0° C. The reaction mixture was allowed to warm up to room temperature and stirred for 10 min. The mixture was cooled to 0° C. and a solution of 4-biphenylcarbaldehyde (2.0 g, 10.98 mmol) in THF (9 mL) was added over 20 min. The reaction mixture was allowed to warm up to room temperature and stirred for ˜19 hour. The mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was dissolved/suspended in DCM and filtered through a silica pad and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 80 g, EtOAc/heptane] to provide vinylbiphenyl (1.845 g) as a white solid. LCMS Rt 0.79 min.