Triacetoxyperiodinane → HCID 22398549, compound

HRID 2080605Notes

Reaction equation

HRID 2080605 reaction equation
[F:1][C:2]([F:19])([F:18])[CH:3]([OH:17])[CH2:4][C:5]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[F:19][C:2]([F:1])([F:18])[C:3](=[O:17])[CH2:4][C:5]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 22398651HCID 22398651, compound

Product 1

HCID 22398549HCID 22398549, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.3 g (8.42 mmol) of 1,1,1-trifluoro-4-(4-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol in 40 mL of dichloromethane was added the 4.96 (11.70 mmol) of Dess-Martin periodinane. After 1 hour, the mixture was concentrated and diluted with ether-hexanes (1:9) and filtered through a pad of silica gel, washing with 1:1 ether-hexanes. Use of a second pad of silica gel washing with EtOAc-hexanes (1:9) afforded the title compound as an oil. The product was dried under vacuum to a constant weight of 2 g (85%).

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with ether-hexanes (1:9)
  3. filtrationfiltered through a pad of silica gel
  4. washwashing with 1:1 ether-hexanes

Sources & evidence

ORD record
ord-4d82e7006c54480fb8f1860b52d245d6
Source dataset
uspto-grants-2011_04
Patent number
US07932392B2

Reaction notes

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