Methyl Acrylate → methyl (RS)-5-(3-iodophenyl)-4-(2-methylphenyl)-5-oxopentanoate

反応式

[I:1][C:2]1[CH:3]=[C:4]([C:8](=[O:17])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH:5]=[CH:6][CH:7]=1.[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].CC(C)([O-])C.[K+]>O1CCCC1>[I:1][C:2]1[CH:3]=[C:4]([C:8](=[O:17])[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH2:20][CH2:19][C:18]([O:22][CH3:23])=[O:21])[CH:5]=[CH:6][CH:7]=1

参加物

実験手順

A solution of 1-(3-iodophenyl)-2-(2-methylphenyl)ethanone (3.21 g) in dry tetrahydrofuran (30 mL) is treated with methyl acrylate (0.9 mL) and potassium tertiary butoxide (0.107 g). The reaction mixture is heated at reflux for 18 hours, evaporated and the residue partitioned between ethyl acetate (60 mL) and water (30 mL). The organic phase is dried over magnesium sulphate, evaporated and the residual solid washed with pentane to give methyl (RS)-5-(3-iodophenyl)-4-(2-methylphenyl)-5-oxopentanoate as a fawn coloured solid (3.39 g), m.p. 106-108° C.