Acetic Anhydride → Ethyl 3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylate

HRID 1770109Notes

Reaction equation

HRID 1770109 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6](=[O:18])[C:7]1[CH:12]=[C:11]([F:13])[C:10]([F:14])=[C:9]([O:15][CH3:16])[C:8]=1[F:17])[CH3:2].[CH:20]([O-])([O-])[O:21][CH2:22][CH3:23].C(OC(=O)C)(=O)C>>[CH3:16][O:15][C:9]1[C:8]([F:17])=[C:7]([CH:12]=[C:11]([F:13])[C:10]=1[F:14])[C:6]([C:5](=[CH:20][O:21][CH2:22][CH3:23])[C:4]([O:3][CH2:1][CH3:2])=[O:19])=[O:18]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 10588473Ethyl 3-oxo-3-(2,4,5-trifluoro-3-methoxyphenyl)propanoateHCID 53630039Ethylorthoformate

Product 1

HCID 54548840Ethyl 3-ethoxy-2-(2,4,5-trifluoro-3-methoxybenzoyl)acrylateYield 98.6%

Conditions

Temperature
110 °C

Procedure

A mixture of ethyl-3-methoxy-2,4,5-trifluorobenzoylacetate (500 mg, 1.8 mmol), ethyl orthoformate (0.45 mL, 2.72 mmol) and acetic anhydride (460 mg, 4.5 mmol, 2.5 eq) was stirred at 110° C. for 12 hours and the excess reagents were removed by distillation under high vacuum (0.1 mmHg) to give 590 mg of a yellow-orange oil. This material was used directly in the next step without further purification or characterization.

Workup

  1. customthe excess reagents were removed by distillation under high vacuum (0.1 mmHg)

Sources & evidence

ORD record
ord-3ee6a5d6d6b74eb58ddc853776f7a5b1
Source dataset
uspto-grants-1995_01
Patent number
US05385913

Reaction notes

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