Dimethyl Sulfate → HCID 66926128, compound

HRID 2170792Notes

Reaction equation

HRID 2170792 reaction equation
S(OC)(O[CH3:5])(=O)=O.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH3:20])[N:17]([CH:21]3[C:25](=[O:26])[CH2:24][CH2:23][C:22]3=[O:27])[N:16]=2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:19]=[C:18]([CH3:20])[N:17]([C:21]3[C:22](=[O:27])[CH2:23][CH2:24][C:25]=3[O:26][CH3:5])[N:16]=2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 66926125HCID 66926125, compound

Product 1

HCID 66926128HCID 66926128, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Neat dimethyl sulfate (0.12 ml, 1.3 mmol) was added at room temperature to a vigorously stirred suspension of 2-[3-(4-chloro-phenyl)-5-methyl-pyrazol-1-yl]-cyclopentane-1,3-dione (374 mg, 1.3 mmol) and potassium carbonate (180 mg, 1.3 mmol) in acetone (10 ml). The mixture was then heated to 60° C. for 3 h with continued stirring, then cooled and the solvent removed in vacuo. The residue was partitioned between ethyl acetate (30 ml) and 1M sodium hydroxide solution (20 ml), the layers were separated, and the aqueous phase was further extracted with ethyl acetate (2×20 ml). The combined organics were washed with brine (20 ml), dried over magnesium sulfate and concentrated. The crude product was then purified by flash chromatography (using 20% to 100% EtOAc in DCM) to give 2-[3-(4-chloro-phenyl)-5-methyl-pyrazol-1-yl]-3-methoxy-cyclopent-2-enone (253.2 mg).

Workup

  1. temperaturecooled
  2. customthe solvent removed in vacuo
  3. customThe residue was partitioned between ethyl acetate (30 ml) and 1M sodium hydroxide solution (20 ml)
  4. customthe layers were separated
  5. extractionthe aqueous phase was further extracted with ethyl acetate (2×20 ml)
  6. washThe combined organics were washed with brine (20 ml)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe crude product was then purified by flash chromatography (using 20% to 100% EtOAc in DCM)

Sources & evidence

ORD record
ord-4aff759930d54b418ba73e625b644083
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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