Methanol → Methyl 4-(4-fluoro-3-methylphenyl)-4-oxobutanoate
Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][C:3]=1[CH3:15].OS(O)(=O)=O.[CH3:21]O>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:14])[CH2:9][CH2:10][C:11]([O:13][CH3:21])=[O:12])=[CH:4][C:3]=1[CH3:15]Komponenten
4
Versuchsvorschrift
To a solution of 4-(4-fluoro-3-methylphenyl)-4-oxobutanoic acid in 30 mL methanol was added concentrated H2SO4 (300 mL) at room temperature and the resulting mixture was stirred for 16 h. The mixture was concentrated under reduced pressure and the residue treated with 30 mL water and the resulting mixture extracted with ethyl acetate (3×40 mL). The combined organic layers were washed with brine (2×20 mL) and dried over Na2SO4. The product was isolated by flash column chromatography eluting with 0% to 10% ethyl acetate/hexane gradient solvent to give 568 mg of the title compound as a colorless oil.