Reaction #428817

Reaction equation

THP-phenol

trifluoroacetamide

p-toluenesulfonic acid monohydrate

THF H2O

NaHCO3 brine

→

2,2,2-trifluoro-N-(4-(3-hydroxyphenyl)butyl)acetamide

Conditions

Workup

1. 1
   Otherwere separated
2. 2
   Extractionaqueous layer extracted with EtOAc
3. 3
   WashCombined organic layers were washed with brine
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   OtherPurification by flash chromatography (10%-50% EtOAc-hexanes gradient)

Procedure

A mixture of THP-phenol 136 (0.72 g, 2.08 mmol), 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 treated with aqueous NaHCO3-brine solution, layers were separated and aqueous layer extracted with EtOAc. Combined organic layers were washed with brine and concentrated under reduced pressure. Purification by flash chromatography (10%-50% EtOAc-hexanes gradient) gave 2,2,2-trifluoro-N-(4-(3-hydroxyphenyl)butyl)acetamide as a colorless oil, which was taken into the next step. Yield (0.438 g, 96%).

Source