Methyltriphenylphosphonium chloride → HCID 67317831、化合物

反応式

[Cl-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([Li])CCC.[CH3:27][O:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33]([C:39]([C:41]3[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=3)=O)=[CH:34][CH:35]=[N:36]2)=[CH:31][CH:30]=1>C1COCC1>[CH3:27][O:28][C:29]1[CH:38]=[C:37]2[C:32]([C:33]([C:39]([C:41]3[CH:46]=[CH:45][C:44]([N+:47]([O-:49])=[O:48])=[CH:43][CH:42]=3)=[CH2:2])=[CH:34][CH:35]=[N:36]2)=[CH:31][CH:30]=1

参加物

実験手順

To a mixture of methyltriphenylphosphonium chloride (0.54 g, 1.7 mmol) in THF (10 mL) at −78° C. was added n-butyllithium, 2.5 M in hexanes (0.80 ml, 2.0 mmol). After 20 min, a mixture of (7-methoxyquinolin-4-yl)(4-nitrophenyl)methanone (0.177 g, 0.57 mmol) in THF (5 mL) was slowly added. After 10 min, the mixture was allowed to warm to RT. The reaction was quenched with saturated aqueous NH4Cl. The mixture was diluted with EtOAc and washed with water and brine. After drying the organic fraction with Na2SO4, the solvent was removed in vacuo and the residue purified by silica gel chromatography using 40-100% hexanes:EtOAc to afford 7-methoxy-4-(1-(4-nitrophenyl)vinyl)quinoline as a yellow foam. MS: M+H+=307.1.