Trifluoroacetamide → 2,2,2-trifluoro-N-(4-(3-hydroxyphenyl)butyl)acetamide
Reaktionsgleichung
[F:1][C:2]([F:7])([F:6])[C:3]([NH2:5])=[O:4].O.[C:9]1(C)[CH:14]=[CH:13][C:12](S(O)(=O)=O)=[CH:11][CH:10]=1.[CH2:20]1[CH2:24][O:23][CH2:22][CH2:21]1.O>>[F:1][C:2]([F:7])([F:6])[C:3]([NH:5][CH2:13][CH2:12][CH2:11][CH2:10][C:9]1[CH:24]=[CH:20][CH:21]=[C:22]([OH:23])[CH:14]=1)=[O:4]Komponenten
4
Versuchsvorschrift
A mixture of 107 (0.72 g, 2.08 mmol) and p-toluenesulfonic acid monohydrate (0.366 g) in THF: H2O (3:1, 20 mL) was stirred at room temperature for 3.5 hr. The reaction mixture was partitioned between aqueous NaHCO3-brine solution and EtOAc. Aqueous layer was aextracted with EtOAc. Combined organic layers were washed with brine and concentrated under reduced pressure. Purification by flash chromatography (10% to 50% EtOAc-hexanes gradient) gave 2,2,2-trifluoro-N-(4-(3-hydroxyphenyl)butyl)acetamide as a colorless oil. Yield (0.438 g, 96%).