Triacetoxyperiodinane → HCID 178458280, compound

HRID 1433205Notes

Reaction equation

HRID 1433205 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:29]=[CH:28][C:6]([O:7][CH2:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[CH:24]([OH:27])[CH2:25][CH3:26])=[CH:17][C:11]=3[N:10]=2)=[CH:5][CH:4]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:31][C:2]([F:1])([F:30])[C:3]1[CH:29]=[CH:28][C:6]([O:7][CH2:8][C:9]2[NH:13][C:12]3[CH:14]=[CH:15][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[C:24](=[O:27])[CH2:25][CH3:26])=[CH:17][C:11]=3[N:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 178458281HCID 178458281, compound2×

Product 1

HCID 178458280HCID 178458280, compoundYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-propan-1-ol (0.100 g, 0.235 mmol, Example 9, Compound 143) in CH2Cl2 (3 mL) was added Dess-Martin periodinane (0.159 g, 0.375 mmol). After stirring at rt for 2 hours, The reaction mixture was concentrated, and the residue was purified by chromatography (silica, hexanes: EtOAc, 2:1) to afford the title compound as a white solid (0.087 g, 87%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography (silica, hexanes: EtOAc, 2:1)

Sources & evidence

ORD record
ord-1baf504ae45a416983543f72b1e83758
Source dataset
uspto-grants-2009_11
Patent number
US07612211B2

Reaction notes

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