Dimethyl Sulfoxide → HCID 17989157, compound

HRID 1869371Notes

Reaction equation

HRID 1869371 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([CH3:20])([CH3:19])[CH2:10][C:11]([C:15]([F:18])([F:17])[F:16])([OH:14])[CH2:12][OH:13].ClCCl.CS(C)=O.[Cl-].[NH4+]>CC(OC)(C)C.C(N(CC)CC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([CH3:20])([CH3:19])[CH2:10][C:11]([OH:14])([C:15]([F:16])([F:17])[F:18])[CH:12]=[O:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 25517Ammonium ChlorideHCID 179891694-(2,5-Difluorophenyl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol

Product 1

HCID 17989157HCID 17989157, compoundYield 85.6%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

800 mg (2.8 mmol) of 4-(2,5-difluorophenyl)-4-methyl-2-trifluoromethyl-pentane-1,2-diol is introduced into 20 ml of dichloromethane, and at 0° C., 9.5 ml of DMSO and 1.95 ml of triethylamine are added. The solution is slowly mixed with 1.34 g (8.4 mmol) of SO3-pyridine complex, and it is stirred for 2 hours at 0° C. The mixture is dispersed between saturated ammonium chloride solution and MTBE, the phases are separated, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with water and saturated NaCl solution and dried with NaSO4. It is concentrated by evaporation and chromatographed on silica gel with hexane/ethyl acetate (30%). 710 mg of the desired product is obtained.

Workup

  1. additionThe solution is slowly mixed with 1.34 g (8.4 mmol) of SO3-pyridine complex, and it
  2. customthe phases are separated
  3. extractionthe aqueous phase is extracted with MTBE
  4. washThe combined organic phases are washed with water and saturated NaCl solution
  5. dry with materialdried with NaSO4
  6. concentrationIt is concentrated by evaporation
  7. customchromatographed on silica gel with hexane/ethyl acetate (30%)

Sources & evidence

ORD record
ord-21f3a06b0c284c378d69c46ea5c9436e
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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