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

HRID 1641470Notes

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].FC(F)(F)C(=O)CC(O)=O.[CH:23](OCC)(OCC)[O:24][CH2:25][CH3:26].C(OC(=O)C)(=O)C>>[CH2:25]([O:24][CH:23]=[C:5]([C:6](=[O:11])[C:7]([F:10])([F:8])[F:9])[C:4]([O:3][CH2:1][CH3:2])=[O:12])[CH3:26]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 31214Ethyl orthoformate

HCID 86640096HCID 86640096, compound

Product 1

HCID 4685753Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoateYield 90%

Conditions

Temperature: 120 °C

Procedure

In a 500 ml four-necked flask with stirrer, 78.3 g (0.425 mol) of trifluoroacetoacetate ethyl-(4,4,4-trifluoro)-3-oxobutyrate, 103.3 g (0.638 mol) of triethyl orthoformate and 130.0 g (1.275 mol) of acetic anhydride were mixed and heated at 120° C. for 6 hours. Then, at atmospheric pressure, initially the low-boiling components were removed and the product was then distilled under reduced pressure over a column. This gave 91.8 g (yield 90%) of the title compound as a colorless liquid of a purity>98%.

Workup

customThen, at atmospheric pressure, initially the low-boiling components were removed
distillationthe product was then distilled under reduced pressure over a column

Sources & evidence

ORD record: ord-4f08dc3c09544619abb77bf2aca29ec0
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08115012B2

Reaction notes

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