Dimethyl Sulfoxide → 4-(4-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

HRID 2118068Notes

Reaction equation

HRID 2118068 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:29])([CH3:28])[CH2:19][C:20]([OH:27])([C:23]([F:26])([F:25])[F:24])[CH2:21][OH:22])=[C:14]([O:30][CH3:31])[CH:13]=1.C(N(CC)CC)C>ClCCl.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:29])([CH3:28])[CH2:19][C:20]([OH:27])([C:23]([F:26])([F:25])[F:24])[CH:21]=[O:22])=[C:14]([O:30][CH3:31])[CH:13]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 219488394-(4-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentan-1-ol

Product 1

HCID 219489374-(4-Chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanalYield 96.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

854.6 mg (6.733 mmol) of oxalyl chloride in 14.5 ml of dichloromethane is introduced into a heated flask. At −70° C., 1.05 ml of DMSO, dissolved in 3 ml of dichloromethane, is added in drops, and the batch is stirred for five more minutes. Then, 2 g (6.12 mmol) of 4-(4-chloro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-pentan-1-ol, dissolved in six milliliters of dichloromethane, is added in drops. After 20 minutes of stirring, the batch is carefully mixed with 4.24 ml (30.61 mmol) of triethylamine, specifically in a temperature range of between −70 and −60° C. After five minutes of stirring at −70° C., the reaction mixture is allowed to slowly reach room temperature. 25 ml of water is added, and the batch is stirred for one more hour at room temperature. After phase separation, the aqueous phase is shaken once with 100 ml of dichloromethane. The combined organic extracts are washed with 1% sulfuric acid, 5% sodium bicarbonate solution and brine. According to the conventional procedures, 1.92 g (96.9%) of the desired aldehyde is obtained, which is incorporated in crude form into the next stage.

Workup

  1. additionis added in drops
  2. additionis added in drops
  3. stirringAfter 20 minutes of stirring
  4. stirringAfter five minutes of stirring at −70° C.
  5. customis allowed to slowly reach room temperature
  6. stirringthe batch is stirred for one more hour at room temperature
  7. customAfter phase separation
  8. stirringthe aqueous phase is shaken once with 100 ml of dichloromethane
  9. washThe combined organic extracts are washed with 1% sulfuric acid, 5% sodium bicarbonate solution and brine

Sources & evidence

ORD record
ord-dd5848a2e61b4aa9856dc44de71ae071
Source dataset
uspto-grants-2008_10
Patent number
US07442794B2

Reaction notes

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