Ethyl orthoformate → Ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)3-ethoxyacrylate

HRID 1081393Notes

Reaction equation

HRID 1081393 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([CH3:11])[C:3]=1[C:12](=[O:19])[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].[CH:20](OCC)(OCC)[O:21][CH2:22][CH3:23]>C(OC(=O)C)(=O)C>[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([CH3:11])[C:3]=1[C:12]([C:13](=[CH:20][O:21][CH2:22][CH3:23])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:19]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 14774100Ethyl 6-methyl-2,3,4,5-tetrafluorobenzoylacetate

Product 1

HCID 54293321Ethyl 2-(2-methyl-3,4,5,6-tetrafluorobenzoyl)3-ethoxyacrylateYield 93.6%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 8.1 g (29.1 mmol) of ethyl 3-(2, 3,4,5-tetrafluoro-6-methylphenyl)-β-oxopropanoate, 7.2 g (43.3 mmol) of triethyl orthoformate, and 70 mL of acetic anhydride was refluxed for 3.5 hours. The solution was cooled to room temperature and concentrated under high vacuum to give 9.1 g of the title compound. The product was used as is in the next step.

Workup

  1. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-112a784f8ed246118c2623f602fc41d8
Source dataset
uspto-grants-1996_12
Patent number
US05585491

Reaction notes

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