Methyl 4-oxo-4-(4-phenoxyphenyl)but-2-enoate → HCID 13276507, compound
Reaction equation
[O:1]([C:8]1[CH:21]=[CH:20][C:11]([C:12]([CH:14]=[CH:15][C:16]([O:18][CH3:19])=[O:17])=[O:13])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([OH:25])(=[S:24])[CH3:23]>C(OCC)C>[C:22]([S:24][CH:15]([CH2:14][C:12](=[O:13])[C:11]1[CH:20]=[CH:21][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][CH:10]=1)[C:16]([O:18][CH3:19])=[O:17])(=[O:25])[CH3:23]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2.82 g of methyl 3-(4-phenoxybenzoyl)acrylate were dissolved in 30 ml of diethyl ether, then 1.5 ml of thioacetic acid were added. The mixture was stirred for 3 hours. The reaction mixture was washed, in turn, with water, a saturated aqueous solution of sodium hydrogencarbonate and water and then dried over magnesium sulfate. The diethyl ether was removed by distillation under reduced pressure. The residue was purified first by silica gel column chromatography, eluted with a mixture of hexane and diethyl ether, then by recrystallization from a mixture of hexane and diethyl ether to give 2.91 g of methyl 2-acetylthio-3-(4-phenoxybenzoyl)-propionate.