Trimethyl orthoformate → 5-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 869449Notes

Reaction equation

HRID 869449 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[CH:11](OC)(OC)[O:12][CH3:13]>>[CH3:11][O:12][CH:13]=[C:5]1[C:6](=[O:8])[O:7][C:2]([CH3:10])([CH3:1])[O:3][C:4]1=[O:9]

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 1521115-(Methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Procedure

A mixture of 2,2-dimethyl-1,3-dioxane-4,6-dione (D-2) (10.0 g, 70 mmol, 1.0 eq) in trimethyl orthoformate (100 mL, 365 mmol, 5.0 eq) is stirred at reflux for 3 h. The resulting mixture is cooled to RT and concentrated in vacuo. The residue is triturated with diethyl ether and then filtered. The filter cake is washed with cooled diethyl ether and dried in vacuo to afford the product, 5-(methoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (D-3).

Workup

  1. temperatureat reflux for 3 h
  2. concentrationconcentrated in vacuo
  3. customThe residue is triturated with diethyl ether
  4. filtrationfiltered
  5. washThe filter cake is washed with cooled diethyl ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-fede49f6e484427daa485440489697b4
Source dataset
uspto-grants-2015_03
Patent number
US08969363B2

Reaction notes

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