Dimethyl Sulfate → 6-ETHYL-4-METHOXY-2-PYRANONE

HRID 1252720Notes

Reaction equation

HRID 1252720 reaction equation
[OH:1][C:2]1([CH2:9][CH3:10])[CH:7]=[CH:6][O:5][C:4](=O)C1.S([O:16][CH3:17])(OC)(=O)=O.[C:18](=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:4][O:5][C:6]1[CH:7]=[C:2]([CH2:9][CH3:10])[O:1][C:17](=[O:16])[CH:18]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 20139208HCID 20139208, compound

Product 1

HCID 111162626-ETHYL-4-METHOXY-2-PYRANONE

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension of 4-hydroxy-4-ethyl-2-pyrone (360 mg, 0.00257 mol), dimethyl sulphate (0.3 ml) and potassium carbonate (1 gm) in 2-butanone was heated at reflux with stirring for 7 hours. The mixture was cooled, filtered and the filtrate was evaporated to give an oil. This oil was further purified by column chromatography (Whatman LPS-II silica gel, 30% ethyl acetate:pet. ether 30-60) to yield 4-methoxy-6-ethyl-2-pyrone (370 mg), m.p. 54°-55° C., IR (KBr): 1730, 1710, 1650, 1570 cm-1. Anal. calcd. for C8H10O3 : C, 62.33, H, 6.54. Found: C, 62.26, H, 6.55.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate was evaporated
  6. customto give an oil
  7. customThis oil was further purified by column chromatography (Whatman LPS-II silica gel, 30% ethyl acetate:pet. ether 30-60)

Sources & evidence

ORD record
ord-4ff94de0ec0a4dd7a9048fd19a72ef01
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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