Ethyl Acetate → Ethyl 4,4,4-trifluoroacetoacetate

HRID 2280349Notes

Reaction equation

HRID 2280349 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3](OCC)=[O:4].[C:10]([O:13][CH2:14][CH3:15])(=[O:12])[CH3:11].[O-]CC.[Na+]>>[F:1][C:2]([F:9])([F:8])[C:3](=[O:4])[CH2:11][C:10]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 9794Ethyl trifluoroacetateHCID 2723922Sodium ethoxide

Product 1

HCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Conditions

Temperature
62.5 °C

Procedure

Ethyl trifluoroacetate (142.1 g, 1.00 moles) is mixed with ethyl acetate (229.1 g, 2.60 moles) under nitrogen at 5-10° C. Sodium ethoxide (71.5 g, 1.05 moles) is added portion-wise at the same temperature. The addition is exothermic, bringing the temperature gradually to 40-55° C. The mixture is heated to 60-65° C. and kept at that temperature for 3 hours. GC indicates a conversion of 98.8%.

Workup

  1. additionThe addition
  2. customgradually to 40-55° C

Sources & evidence

ORD record
ord-e3b685846dbc4fa5bfe80fb2e3541816
Source dataset
uspto-grants-2015_09
Patent number
US09139507B2

Reaction notes

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