Dimethyl Sulfoxide → HCID 15295201, compound

HRID 2394498Notes

Reaction equation

HRID 2394498 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][CH2:23]3)[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:19])[F:20])=[C:13]([O:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]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 15295201HCID 15295201, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 2-carbomethoxy-4-cyano-4-(3-cyclopentyloxy-4-difluoromethoxyphenyl)cyclohexan-1-one (0.98 g, 2.4 mmole), dimethyl sulfoxide (10 mL), water (0.62 mL) and sodium chloride (0.62 g) under an argon atmosphere was heated at 145° C. for 5 h. The reaction mixture was cooled to room temperature and concentrated. The residue was partitioned between ether and water, the organic layer washed with water, was dried (magnesium sulfate) and the solvent was removed in vacuo. The product was purified by flash chromatography, eluting with 20-30% ethyl acetate/hexanes. The isolated residue was dissolved in ethyl acetate, this was washed twice with dilute sodium hydroxide, once with water, once with brine and then was dried and evaporated to yield a solid (0.2 g, 23.6%): m.p. 76°-78.5° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was partitioned between ether and water
  4. washthe organic layer washed with water
  5. dry with materialwas dried (magnesium sulfate)
  6. customthe solvent was removed in vacuo
  7. customThe product was purified by flash chromatography
  8. washeluting with 20-30% ethyl acetate/hexanes
  9. dissolutionThe isolated residue was dissolved in ethyl acetate
  10. washthis was washed twice with dilute sodium hydroxide, once with water, once with brine
  11. customwas dried
  12. customevaporated

Sources & evidence

ORD record
ord-198b0ffef303444b8b43c24e8a7ef00d
Source dataset
uspto-grants-1998_09
Patent number
US05811455

Reaction notes

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