Ethyl orthoformate → Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturethe reaction heated
- temperatureto reflux for 18 hours
- temperatureThe reaction was cooled
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c4d1ba12b2db4c698f4e8d65ad4744ba
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09163021B2
Reaction notes
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