Acetic Anhydride → Ethyl ethoxymethylene-3-oxo-4,4,4-trifluorobutyrate

HRID 1753087Notes

Reaction equation

HRID 1753087 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])[CH3:2].[C:13]([O:16][C:17](=O)C)(=O)[CH3:14].C(OCC)(OCC)OCC>>[CH2:1]([O:3][C:4](=[O:12])/[C:5](=[CH:17]/[O:16][CH2:13][CH3:14])/[C:6](=[O:11])[C:7]([F:10])([F:8])[F:9])[CH3:2]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 6185754Ethyl ethoxymethylene-3-oxo-4,4,4-trifluorobutyrateYield 96.4%

Procedure

4,4,4-Trifluoro-3-oxo-butyric acid ethyl ester (16 g, 86.4 mmol) was dissolved in acetic anhydride (33.6 g, 329.6 mmol) and triethyl orthoformate (38.4 g, 260 mmol) was added to the mixture. The resultant mixture was refluxed for 18 hours. The mixture was concentrated under reduced pressure to obtain 20 g of 2-[1-Ethoxy-meth-(E)-ylidene]-4,4,4-trifluoro-3-oxo-butyric acid ethyl ester as crude.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c69bb7231c8f41809dd60e5b3613124d
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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