Dimethyl Sulfate → 3-Methoxy-2-methyl-4H-pyran-4-one

HRID 1720041Notes

Reaction equation

HRID 1720041 reaction equation
[CH3:1]OS(OC)(=O)=O.[CH3:8][C:9]1[O:15][CH:14]=[CH:13][C:11](=[O:12])[C:10]=1[OH:16]>[OH-].[K+]>[CH3:1][O:16][C:10]1[C:11](=[O:12])[CH:13]=[CH:14][O:15][C:9]=1[CH3:8]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 8369Maltol

Product 1

HCID 5876933-Methoxy-2-methyl-4H-pyran-4-oneYield 36,749.801%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

Dimethylsulphate (3.8 ml, 5.05 g, 0.04 mmol) was added to a solution of maltol (5.0 g, 0.04 mmol) in 10% aqueous potassium hydroxide (22.5 ml). After stirring for 5h the reaction mixture was extracted into CH2Cl2 (x3). The organic extract was dried (MgSO4) and concentrated under reduced pressure. The residue was chromatographed on silica gel 60 eluting with 60% ethyl acetate in hexane to give the title compound (2.06 g, 37%) as a pale yellow oil; νmax (film) 3080, 1620, and 1580 cm-1 ; δH (CDCl3) 2.3 (3H, s), 3.8 (3H, s), 6.3 (1H, d, J 6 Hz), 7.6 (1H, d, J 6 Hz).

Workup

  1. extractionwas extracted into CH2Cl2 (x3)
  2. extractionThe organic extract
  3. dry with materialwas dried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was chromatographed on silica gel 60 eluting with 60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e2b47e66321c4f2b81f8daca46342c6a
Source dataset
uspto-grants-1996_04
Patent number
US05504076

Reaction notes

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