Ethyl 4,4,4-trifluoroacetoacetate → Diethyl Trifluoroacetylglutarate

HRID 1440455Notes

Reaction equation

HRID 1440455 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 trifluoroacetoacetate (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 min) 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-314cb5b090294bc9a64a729c314677ef
Source dataset
uspto-grants-1996_03
Patent number
US05498776

Reaction notes

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