Triacetoxyperiodinane → 3,5-Dicyclopropyl-4-(trifluoromethoxy)benzaldehyde

HRID 402830Notes

Reaction equation

HRID 402830 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH2:18][OH:19])[CH:7]=[C:8]([CH:15]3[CH2:17][CH2:16]3)[C:9]=2[O:10][C:11]([F:14])([F:13])[F:12])[CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:1]1([C:4]2[CH:5]=[C:6]([CH:7]=[C:8]([CH:15]3[CH2:17][CH2:16]3)[C:9]=2[O:10][C:11]([F:12])([F:13])[F:14])[CH:18]=[O:19])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 66765168(3,5-Dicyclopropyl-4-(trifluoromethoxy)phenyl)methanol

Product 1

HCID 772308733,5-Dicyclopropyl-4-(trifluoromethoxy)benzaldehydeYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[3,5-Dicyclopropyl-4-(trifluoromethoxy)phenyl]methanol (190 mg, 0.698 mmol) was dissolved in DCM (6 mL) and Dess-Martin periodinane (444 mg, 1.05 mmol) was added. The mixture was stirred for 1 hour at room temperature. The mixture was evaporated in vacuo and the residue was purified by silica gel chromatography (0-10% EtOAc/hexanes) to yield the title compound as a clear oil (174 mg).

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel chromatography (0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-55bc0f233a10477499c22c598c42533b
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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