Ethanol → 5-ethoxy-2-methyl-2H-pyran-3(6H)-one

HRID 478308Notes

Reaction equation

HRID 478308 reaction equation
[CH3:1][CH:2]1[C:7](=[O:8])[CH2:6][C:5](=[O:9])[CH2:4][O:3]1.[CH2:10](O)[CH3:11]>S(=O)(=O)(O)O>[CH2:10]([O:9][C:5]1[CH2:4][O:3][CH:2]([CH3:1])[C:7](=[O:8])[CH:6]=1)[CH3:11]

Participants

4

Reactant 2

HCID 702EthanolHCID 234974742-methyl-2H-pyran-3,5(4H,6H)-dione

Product 1

HCID 180010055-ethoxy-2-methyl-2H-pyran-3(6H)-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

The product from Example 84C (3.0 g, 23 mmol) was dissolved in ethanol (50 mL), treated with concentrated sulfuric acid (5 drops), heated to reflux for 3 hours and concentrated. The residue was purified by chromatography eluting with 10:1 and then 5:1 and then 2:1 hexane:ethyl acetate to provide the title compound as the faster moving isomer.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography
  5. washeluting with 10:1

Sources & evidence

ORD record
ord-13a9e2ec99674901be2c87a3f05fe087
Source dataset
uspto-grants-2003_11
Patent number
US06642222B2

Reaction notes

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