4-(2,3-Dihydrobenzofuran-7-yl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol → 4-(2,3-Dihydrobenzofur-7-yl)-1,1,1-trifluoro-4-methyl-2-pentanone

HRID 400616Notes

Reaction equation

HRID 400616 reaction equation
[O:1]1[C:5]2[C:6]([C:10]([CH3:21])([CH3:20])[CH2:11][C:12]([C:16]([F:19])([F:18])[F:17])([OH:15])CO)=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1>CO>[O:1]1[C:5]2[C:6]([C:10]([CH3:21])([CH3:20])[CH2:11][C:12](=[O:15])[C:16]([F:18])([F:19])[F:17])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 469394814-(2,3-Dihydrobenzofuran-7-yl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol

Product 1

HCID 469392134-(2,3-Dihydrobenzofur-7-yl)-1,1,1-trifluoro-4-methyl-2-pentanoneYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-(2,3-dihydrobenzofuran-7-yl)-4-methyl-2-trifluoromethylpentane-1,2-diol (24.0 g, 78.9 mmol) and NaIO4 (84.3 g, 394 mmol) in 360 mL of methanol was stirred at room temperature overnight. The resulting mixture was filtered through pad of CELITE® filter aid and the filter cake was washed with three 100 mL portions of methanol. The filtrate was concentrated in vacuo, taken up in hexanes, filtered again, and concentrated in vacuo to give 21.4 g of 4-(2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one as colorless oil (quantitative yield), which was used without purification.

Workup

  1. filtrationThe resulting mixture was filtered through pad of CELITE®
  2. filtrationfilter aid
  3. washthe filter cake was washed with three 100 mL portions of methanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. filtrationfiltered again
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a70fbb6227044e0690436f7b5b60dc92
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

Loading…