Acetic Anhydride → Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate

HRID 1584841Notes

Reaction equation

HRID 1584841 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:13][C:14]([O:16][C:17](C)=O)=O>>[CH2:14]([O:16][CH:17]=[C:4]([C:3]([C:2]([F:11])([F:12])[F:1])=[O:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 4685753Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoateYield 98%

Procedure

A solution of ethyl 4,4,4-trifluoroacetoacetate (46 g, 0.25 mol) triethyl orthoformate (74 g, 0.50 mol) and Ac2O (77 g, 0.75 mol) was heated at 120-140° C. for 7 h. The mixture was concentrated and distilled to give the title compound in a 98% yield (58.6 g); b.p. 80-90° C., 1.5 mm/Hg.

Workup

  1. concentrationThe mixture was concentrated
  2. distillationdistilled

Sources & evidence

ORD record
ord-8ffdd7ee68e846c8bcbc915532cc2002
Source dataset
uspto-grants-1999_08
Patent number
US05935966

Reaction notes

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