Dimethyl Sulfoxide → HCID 21948865, compound

HRID 2215484Notes

Reaction equation

HRID 2215484 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])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([CH3:29])([CH3:28])[CH2:19][C:20]([OH:27])([C:23]([F:25])([F:26])[F:24])[CH:21]=[O:22])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 219488444-(4-Chlorophenyl)-4-methyl-2-(trifluoromethyl)pentane-1,2-diol

Product 1

HCID 21948865HCID 21948865, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

0.674 ml of oxalyl chloride in 16.8 ml of dichloromethane is mixed at −78° C. with 1.15 ml of DMSO in 3.4 ml of dichloromethane. After 5 minutes, 2 g of 4-(4-chlorophenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentan-1-ol in 6.8 ml of dichloromethane is added in drops at −78° C. After 15 minutes, it is mixed with 4.7 ml of triethylamine and slowly heated to room temperature. It is washed with water and brine, dried with sodium sulfate and concentrated by evaporation in a vacuum. After chromatography on silica gel (hexane/ethyl acetate 98:2), 1.07 g of 4-(4-chlorophenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)-pentanal is obtained as a colorless oil. 300 mg thereof was heated with 194 mg of 5-amino-2-methylquinoline in 9 ml of glacial acetic acid for 4.5 hours to 130° C. After toluene is added, it is concentrated by evaporation in a vacuum. The residue is taken up in methanol and mixed at 0° C. with 153 mg of sodium borohydride. It is allowed to stir for 5 hours at room temperature, and water is added. The batch is concentrated by evaporation in a vacuum, extracted with ethyl acetate, washed with water and brine, dried with sodium sulfate and concentrated by evaporation in a vacuum. After chromatography on silica gel (hexane/ethyl acetate 100:0->85:15), 163 mg of the title compound is obtained as a yellow solid.

Workup

  1. waitAfter 15 minutes
  2. washIt is washed with water and brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-d95df2d53ad54800b6184e68b158bb00
Source dataset
uspto-grants-2006_09
Patent number
US07109212B2

Reaction notes

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