Triacetoxyperiodinane → 2,2,2-Trifluoro-1-(5-(methylsulfonyl)-[1,1'-biphenyl]-2-yl)ethanone

HRID 1499244Notes

Reaction equation

HRID 1499244 reaction equation
[F:1][C:2]([F:22])([F:21])[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[OH:4].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:22][C:2]([F:1])([F:21])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:6]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:4]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 1179420722,2,2-Trifluoro-1-(5-(methylsulfonyl)-[1,1'-biphenyl]-2-yl)ethanol

Product 1

HCID 1179521742,2,2-Trifluoro-1-(5-(methylsulfonyl)-[1,1'-biphenyl]-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2,2,2-trifluoro-1-(5-(methylsulfonyl)-[1,1′-biphenyl]-2-yl)ethanol (720 mg, 2.2 mmol)) in CH2Cl2 (50 mL) was added Dess-Martin periodinane (1.1 g, 2.6 mmol). The reaction was stirred for 2 h at RT, then concentrated in vacuo and purified directly on normal phase silica gel to provide 2,2,2-trifluoro-1-(5-(methylsulfonyl)-[1,1′-biphenyl]-2-yl)ethanone as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. custompurified directly on normal phase silica gel

Sources & evidence

ORD record
ord-218687df27a641efa92aeecadaa9194e
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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