Dimethyl Sulfoxide → HCID 15295202, compound

HRID 2399417Notes

Reaction equation

HRID 2399417 reaction equation
C([CH:5]1[CH2:10][C:9]([C:27]#[N:28])([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH:22]3[CH2:26][CH2:25][CH2:24]C3)[CH:12]=2)[CH2:8][CH2:7][C:6]1=[O:29])(OC)=O.CS(C)=O.[Cl-].[Na+]>O>[C:27]([C:9]1([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:18]([F:20])[F:19])=[C:13]([O:21][CH2:22][CH:26]3[CH2:24][CH2:25]3)[CH:12]=2)[CH2:10][CH2:5][C:6](=[O:29])[CH2:7][CH2:8]1)#[N:28]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 10364019Methyl 5-cyano-5-[3-(cyclopentyloxy)-4-(difluoromethoxy)phenyl]-2-oxocyclohexanecarboxylate

Product 1

HCID 15295202HCID 15295202, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-carbomethoxy-4-cyano-4-(3-cyclopentyloxy-4-difluoromethoxyphenyl)cyclohexan-1-one (0.5 g, 1.27 mmol), dimethyl sulfoxide (10 mL), water (1 mL) and sodium chloride (0.5 g) under an argon atmosphere was heated at 145°-150° C. for 4.5 h. The reaction mixture was cooled to room temperature and concentrated. The residue was partitioned between ethyl acetate and water, extracted twice with ethyl acetate,the organic layer was washed twice with water and once with brine, was dried (sodium sulfate) and the solvent was removed in vacuo. The product was purified by flash chromatography, eluting with 20-25% ethyl acetate/hexanes,and the resultant solid was triturated with ether/hexane and then with cold ether to provide a solid (0.22 g, 51.6%): m.p. 85.5-86.5° C.

Workup

  1. temperaturewas heated at 145°-150° C. for 4.5 h
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and water
  4. extractionextracted twice with ethyl acetate,the organic layer
  5. washwas washed twice with water and once with brine
  6. dry with materialwas dried (sodium sulfate)
  7. customthe solvent was removed in vacuo
  8. customThe product was purified by flash chromatography
  9. washeluting with 20-25% ethyl acetate/hexanes,and the resultant solid
  10. customwas triturated with ether/hexane

Sources & evidence

ORD record
ord-86913c7fab364fafaeee86fca2cf46f0
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

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