Dimethyl Sulfate → HCID 13245003, compound

HRID 260720Notes

Reaction equation

HRID 260720 reaction equation
[O:1]=[C:2]([CH3:12])[CH2:3][CH:4]1[CH:6]([C:7]([OH:9])=[O:8])[C:5]1([CH3:11])[CH3:10].[C:13](=O)(O)[O-].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[O:1]=[C:2]([CH3:12])[CH2:3][CH:4]1[CH:6]([C:7]([O:9][CH3:13])=[O:8])[C:5]1([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 6497Dimethyl Sulfate2×HCID 516893Potassium BicarbonateHCID 12786087HCID 12786087, compound

Product 1

HCID 13245003HCID 13245003, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10 g of 3-(2-oxopropyl)-2,2-dimethyl-cyclopropane carboxylic acid in 100 ml of acetone were heated to 30° C. to 34° C. in the presence of 7.35 g of potassium bicarbonate and 5 ml of dimethyl sulfate. After 4 hours of stirring, 0.85 ml of dimethyl sulfate were added and the reaction medium was held at 30° to 34° C. for 20 hours. After filtration, the product was taken up in ethyl ether and the solvent was evaporated. The residue was chromatographed on silica (eluant: hexane - ethyl acetate 8-2) to obtain 10.43 g of the expected product.

Workup

  1. waitthe reaction medium was held at 30° to 34° C. for 20 hours
  2. filtrationAfter filtration
  3. customthe solvent was evaporated
  4. customThe residue was chromatographed on silica (eluant: hexane - ethyl acetate 8-2)

Sources & evidence

ORD record
ord-9f45da709d1142c39aa2d8ffc46af7d6
Source dataset
uspto-grants-1996_06
Patent number
US05530022

Reaction notes

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