Water → 5-(3-(Trifluoromethyl)phenyl)furfural

HRID 1257477

Reaction equation

HRID 1257477 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:4]=[C:5]([C:9]2[O:13][C:12]([CH2:14][OH:15])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.O>ClCCl>[F:16][C:2]([F:1])([F:17])[C:3]1[CH:4]=[C:5]([C:9]2[O:13][C:12]([CH:14]=[O:15])=[CH:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 159087TriacetoxyperiodinaneHCID 7782745{5-[3-(Trifluoromethyl)phenyl]furan-2-yl}methanol

Product 1

HCID 7218375-(3-(Trifluoromethyl)phenyl)furfural

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the compound (0.45 g) obtained in Example 130b in dichloromethane (4 mL) was cooled in an ice bath, and Dess-martin reagent (0.94 g) was added. After stirring at room temperature for 1 hr, water was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium thiosulfate solution, dried over magnesium sulfate, and concentrated under reduced pressure to give a crude title compound.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic layer was washed with saturated aqueous sodium thiosulfate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c14da28565a44c74a7cdb7c0a1816852
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Linked notes

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