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

HRID 1443126Notes

Reaction equation

HRID 1443126 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 can slowly come to room temperature. 25 ml of water is added, and the batch is stirred for another 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 I% sulfuric acid, 5% sodium bicarbonate solution and brine. According to the usual procedure, 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. customcan slowly come to room temperature
  6. stirringthe batch is stirred for another 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 I% sulfuric acid, 5% sodium bicarbonate solution and brine

Sources & evidence

ORD record
ord-d67e649b623440328b06c437cd4bf067
Source dataset
uspto-grants-2010_02
Patent number
US07659297B2

Reaction notes

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