2,2,2-Trifluoroethanol → 2-Phenyl-2-(2,2,2-trifluoroethoxy)ethan-1-ol

HRID 870469Notes

Reaction equation

HRID 870469 reaction equation
[C:1]1([C@H:7]2[CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:10][C:11]([F:15])([F:14])[CH2:12][OH:13]>>[C:1]1([CH:7]([O:13][CH2:12][C:11]([F:15])([F:14])[F:10])[CH2:9][OH:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 114946(S)-styrene oxide

Product 1

HCID 866847062-Phenyl-2-(2,2,2-trifluoroethoxy)ethan-1-olYield 22%

Procedure

Into a 25-mL round-bottom flask was placed (2S)-2-phenyloxirane (1 g, 8.32 mmol, 1.00 equiv), 2,2,2-trifluoroethan-1-ol (5 mL) and bis[(trifluoromethane)sulfonyloxy]alumanyl trifluoromethanesulfonate (197 mg, 0.42 mmol, 0.05 equiv). The resulting solution was stirred for 2 h at room temperature. The mixture was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20). Purification afforded 410 mg (22%) of 2-phenyl-2-(2,2,2-trifluoroethoxy)ethan-1-ol as a colorless oil.

Workup

  1. customInto a 25-mL round-bottom flask was placed
  2. concentrationThe mixture was concentrated under vacuum
  3. customPurification

Sources & evidence

ORD record
ord-58de7789f1654d24bf776900e47928bd
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Reaction notes

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