Dimethyl Sulfoxide → 3-(4-Fluorophenyl)-3-methylbutyraldehyde

HRID 400624Notes

Reaction equation

HRID 400624 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:23])([CH3:22])[CH2:19][CH2:20][OH:21])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[F:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([CH3:23])([CH3:22])[CH2:19][CH:20]=[O:21])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 600268633-(4-Fluorophenyl)-3-methylbutan-1-ol

Product 1

HCID 214680123-(4-Fluorophenyl)-3-methylbutyraldehydeYield 33.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

12 mL of a 2 M solution of oxalyl chloride in dichloromethane was diluted with 19 mL of dichloromethane and cooled on a dry ice/acetone bath. To this solution was added a dropwise a solution of 3.6 mL of DMSO in 16 mL of dichloromethane. After 10 minutes, a solution of 3-(4-fluorophenyl)-3-methylbutan-1-ol (3.6 g, 19.8 mmol) in 12 mL of dichloromethane was added and the mixture was stirred for 15 minutes. 14 mL of triethylamine was then added, the cooling bath was removed, and the reaction mixture was allowed to warm to room temperature and was quenched with water and diluted with hexanes. The organic layer was separated, washed with water, dried, filtered, and concentrated in vacuo. The residue was purified by chromatography over silica gel (eluent: hexanes to hexanes-dichloromethane (9:1), gradient) to give 1.2 g of 3-(4-fluorophenyl)-3-methylbutyraldehyde as an oil.

Workup

  1. temperaturecooled on a dry ice/acetone bath
  2. customthe cooling bath was removed
  3. customwas quenched with water
  4. additiondiluted with hexanes
  5. customThe organic layer was separated
  6. washwashed with water
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by chromatography over silica gel (eluent: hexanes to hexanes-dichloromethane (9:1), gradient)

Sources & evidence

ORD record
ord-948dc018cf1e42af8b0a0232375e902c
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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