Ethyl orthoformate → Ethyl 3-ethoxy-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate

HRID 476774Notes

Reaction equation

HRID 476774 reaction equation
[Cl:1][C:2]1[C:3]([F:18])=[C:4]([C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[CH:19](OCC)(OCC)[O:20][CH2:21][CH3:22]>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[C:3]([F:18])=[C:4]([CH:5]=[C:6]([F:9])[C:7]=1[F:8])[C:10]([C:11](=[CH:19][O:20][CH2:21][CH3:22])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:17]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 10934859Ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate

Product 1

HCID 54402571Ethyl 3-ethoxy-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 2.3 g (8.2 mmol) of ethyl β-(3-chloro-2,4,5-trifluorophenyl)-β-oxopropionate, 2 ml of triethyl orthoformate, and 20 ml of acetic anhydride is refluxed for 21/2 hours. The reaction mixture is cooled to room temperature and concentrated to give 2.7 g of the title compound as a red oil.

Workup

  1. temperatureis refluxed for 21/2 hours
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d71f6285e8d04eb19ada09670b178061
Source dataset
uspto-grants-1989_12
Patent number
US04885386

Reaction notes

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