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

HRID 2098518Notes

Reaction equation

HRID 2098518 reaction equation
[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]

Participants

4

Reactant 3

HCID 67717TrifluoroacetamideHCID 521998p-Toluenesulfonic acid monohydrateHCID 21881883Oxolane--water (1/1)

Product 1

HCID 866284752,2,2-trifluoro-N-(4-(3-hydroxyphenyl)butyl)acetamide

Procedure

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%).

Workup

  1. customThe reaction mixture was partitioned between aqueous NaHCO3-brine solution and EtOAc
  2. washCombined organic layers were washed with brine
  3. concentrationconcentrated under reduced pressure
  4. customPurification by flash chromatography (10% to 50% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-093b07581412490a895c6b64ae6ddea5
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

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