Ethyl trifluoroacetate → 5,5-Diethoxy-1,1,1-trifluoro-pent-3-yn-2-one

HRID 1952573Notes

Reaction equation

HRID 1952573 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[CH:6])[CH3:2].[Li]CCCC.C([O:17][C:18](=O)[C:19]([F:22])([F:21])[F:20])C>C1COCC1>[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[C:5]#[C:6][C:18](=[O:17])[C:19]([F:22])([F:21])[F:20])[CH3:2]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 662853,3-DiethoxypropyneHCID 178418339Butyllithium

Product 1

HCID 109770935,5-Diethoxy-1,1,1-trifluoro-pent-3-yn-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,3-Diethoxy-propyne (0.98 g, 7.64 mmol) in THF (20 ml) was cooled to −78 C under Ar. A solution of n-BuLi (2.0M in cyclohexane, 4.2 ml, 8.40 mmol) was added. After 30 min., Trifluoroacetic acid ethyl ester (1.19 g, 8.40 mmol) was added. After 1 h, the reaction was quenched by dilution with 1N HCl, warmed to room temperature and extracted into EtOAc. The organic layer was washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography (0-40% EtOAc in Hexanes) to give product, 0.51 g (30%).

Workup

  1. temperaturewas cooled to −78 C under Ar
  2. waitAfter 1 h
  3. customthe reaction was quenched by dilution with 1N HCl
  4. extractionextracted into EtOAc
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (0-40% EtOAc in Hexanes)
  10. customto give product, 0.51 g (30%)

Sources & evidence

ORD record
ord-f8e6773304a54db194ed875d379c60cd
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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