Ethyl orthoformate → Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate

HRID 1753101Notes

Reaction equation

HRID 1753101 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].[CH2:13]([O:15][CH:16](OCC)OCC)[CH3:14]>C(OC(=O)C)(=O)C>[CH2:13]([O:15]/[CH:16]=[C:4](/[C:3](=[O:10])[C:2]([F:11])([F:12])[F:1])\[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:14]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 2737179Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of ethyl 4,4,4-trifluoro-3-oxobutanoate (20 g, 108.63 mmol) in acetic anhydride (39 mL) was added triethylorthoformate (54.2 mL, 325.89 mmol) and the reaction heated to reflux for 18 hours. The reaction was cooled, concentrated in vacuo and used directly in the next step.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c4d1ba12b2db4c698f4e8d65ad4744ba
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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