Selenium Dioxide → 2-Methoxymethyl-2,5,5-trimethylfuran-3,4-dione

HRID 1191579Notes

Reaction equation

HRID 1191579 reaction equation
[Se](=O)=O.[CH3:4][O:5][CH2:6][C:7]1([CH3:15])[O:11][C:10]([CH3:13])([CH3:12])[C:9](=[O:14])[CH2:8]1.C[O:17]CC1(C)C(=O)CC(C)(C)O1>O1CCOCC1>[CH3:4][O:5][CH2:6][C:7]1([CH3:15])[C:8](=[O:17])[C:9](=[O:14])[C:10]([CH3:12])([CH3:13])[O:11]1

Participants

5

Reactant 3

HCID 24007Selenium DioxideHCID 594459202-Methoxymethyl-2,5,5-trimethyldihydrofuran-3-oneHCID 594459245-Methoxymethyl-2,2,5-trimethyldihydrofuran-3-one

Product 1

HCID 594459142-Methoxymethyl-2,5,5-trimethylfuran-3,4-dione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A stirred solution of selenium dioxide (2.10 g, 18.91 mmol) in moist dioxane (17 ml, containing 0.5% distilled water by volume) is heated to 100° C., at which point a second (mixed) solution of 5-methoxymethyl-2,2,5-trimethyldihydrofuran-3-one and 2-methoxymethyl-2,5,5-trimethyldihydrofuran-3-one (2.55 g, 14.82 mmol) in moist dioxane (5 ml, containing 0.5% distilled water by volume) is added dropwise over 40 minutes, then further heated at this temperature for 3 hours. After cooling to room temperature the mixture is filtered through diatomaceous earth (washing with diethyl ether) then the solvents are removed at 40° C./50 mbar to give a viscous red-brown oil. This material is purified by bulb to bulb distillation to afford 2-methoxymethyl-2,5,5-trimethylfuran-3,4-dione (2.15 g) as a bright red oil.

Workup

  1. additionis added dropwise over 40 minutes
  2. temperaturefurther heated at this temperature for 3 hours
  3. filtrationis filtered through diatomaceous earth (washing with diethyl ether)
  4. customthe solvents are removed at 40° C./50 mbar
  5. customto give a viscous red-brown oil
  6. distillationThis material is purified by bulb to bulb distillation

Sources & evidence

ORD record
ord-b8882ef4dcca46fcbc9192f46a6cfaf8
Source dataset
uspto-grants-2014_03
Patent number
US08680012B2

Reaction notes

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