Acetic Anhydride → Butanoic acid, 2-(ethoxymethylene)-4,4-difluoro-3-oxo-, ethyl ester

HRID 541056Notes

Reaction equation

HRID 541056 reaction equation
[C:1]([O:4][C:5](=O)C)(=O)[CH3:2].[F:8][CH:9]([F:18])[C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(OCC)(OCC)OCC>>[CH2:1]([O:4][CH:5]=[C:11]([C:10](=[O:17])[CH:9]([F:18])[F:8])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH3:2]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 67697Ethyl 4,4-difluoroacetoacetate

Product 1

HCID 53395411Butanoic acid, 2-(ethoxymethylene)-4,4-difluoro-3-oxo-, ethyl ester

Conditions

Temperature
65 °C

Procedure

Acetic anhydride (3.6 moles) is heated to 100 to 105° C., to which a mixture of crude ethyl difluoroacetoacetate (˜0.96 moles) and triethyl orthoformate (1.8 moles) is added drop-wise. The reaction mixture is kept at 100 to 105° C. for 6 hours. The reaction mixture is cooled to 60 to 70° C. and then concentrated under vacuum to remove excessive acetic anhydride, triethyl orthoformate, and generated ethyl acetate. A pale brown liquid is obtained.

Workup

  1. additionis added drop-wise
  2. concentrationconcentrated under vacuum
  3. customto remove excessive acetic anhydride, triethyl orthoformate
  4. customA pale brown liquid is obtained

Sources & evidence

ORD record
ord-3c62f9b4714a4933a6e91d01654625fa
Source dataset
uspto-grants-2014_10
Patent number
US08871947B2

Reaction notes

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