Triacetoxyperiodinane → HCID 66966185, compound

HRID 1515062Notes

Reaction equation

HRID 1515062 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([CH:17]([OH:22])[C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:12]2[CH:13]=[C:14]([C:17](=[O:22])[C:18]([F:19])([F:20])[F:21])[CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66965827HCID 66965827, compound

Product 1

HCID 66966185HCID 66966185, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,6-dimethylphenyl)-6-(2,2,2-trifluoro-1-hydroxyethyl)-benzoimidazole-1-carboxylic acid tert-butyl ester (475 mg) in methylene chloride (15 mL) was added Dess-Martin reagent (527 mg) and the mixture was stirred at ambient temperature for 18 h. The mixture was washed with water and sodium bicarbonate solution then was dried over sodium sulfate. The solvent was removed under reduced pressure to give 2-(2,6-dimethylphenyl)-6-(2,2,2-trifluoroacetyl)-benzoimidazole-1-carboxylic acid tert-butyl ester as a gummy solid. The material was used directly in the next reaction.

Workup

  1. washThe mixture was washed with water and sodium bicarbonate solution
  2. dry with materialthen was dried over sodium sulfate
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f5162e0fc630433083dbadf1e0005396
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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