Acetic Anhydride → Methyl 2-(methoxymethylidene)-3-oxopentanoate

HRID 1534498Notes

Reaction equation

HRID 1534498 reaction equation
[C:1]([CH2:5][C:6]([O:8][CH3:9])=[O:7])(=[O:4])[CH2:2][CH3:3].[CH:10](OC)(OC)[O:11][CH3:12].C(OC(=O)C)(=O)C>>[C:1]([C:5](=[CH:10][O:11][CH3:12])[C:6]([O:8][CH3:9])=[O:7])(=[O:4])[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 9005Trimethyl orthoformateHCID 121699Methyl 3-oxovalerate

Product 1

HCID 53662896Methyl 2-(methoxymethylidene)-3-oxopentanoate

Procedure

A mixture of methyl propionylacetate (112.2 g, 0.86 mol), trimethyl orthoformate (188 ml, 1.72 mol) and acetic anhydride (81 ml, 0.86 mol) was heated at reflux for 17 hours, then the volatile material removed in vacuo, finally at 70°/0.3mm. The residue was predominantly methyl 2-propanoyl-3-methoxyacrylate, and was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 17 hours
  3. customthe volatile material removed in vacuo, finally at 70°/0.3mm
  4. customwas used without further purification

Sources & evidence

ORD record
ord-12c713b72b264238b420b4c679e343a6
Source dataset
uspto-grants-1992_02
Patent number
US05089504

Reaction notes

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