Ethyl 4,4,4-trifluoroacetoacetate → Diethyl Trifluoroacetylglutarate

HRID 1886064Notes

Reaction equation

HRID 1886064 reaction equation
CC[O-].[Na+].[F:5][C:6]([F:16])([F:15])[C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].Br[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CCO>[F:5][C:6]([F:15])([F:16])[C:7]([CH:8]([CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:14]

Participants

5

Reactant 3

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 68320Ethyl 3-bromopropionateHCID 2723922Sodium ethoxide

Product 1

HCID 10636762Diethyl TrifluoroacetylglutarateYield 90.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of NaOEt (0.217 mol) in EtOH (prepared from 5.0 g of Na and 220 mL of EtOH) was added ethyl triflouroacetoacetate (40.0 g, 0.217 mol). After 10 min, ethyl 3-bromopropionate (35.0 g, 0.194 mol) was added and the mixture was heated under reflux for 24 h. The reaction mixture was concentrated, taken up in ether, and washed with water. The ether layers were dried (MgSO4) and concentrated to give 50 g of a yellow oil. Distillation (100°-110° C./25 mm) gave 14.0 g (23%) of product as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 h
  3. concentrationThe reaction mixture was concentrated
  4. washwashed with water
  5. dry with materialThe ether layers were dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c520bc7c49634da4ba0fed36d61ddad5
Source dataset
uspto-grants-1992_09
Patent number
US05149699

Reaction notes

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