Potassium Carbonate → Ethyl 4,4,4-trifluoro-2-butynoate

HRID 424820Notes

Reaction equation

HRID 424820 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3](=O)[C:4](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(=O)([O-])[O-].[K+].[K+]>>[CH2:8]([O:7][C:5](=[O:6])[C:4]#[C:3][C:2]([F:30])([F:31])[F:1])[CH3:9]

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 5068679Ethyl 4,4,4-trifluoro-2-(triphenylphosphoranylidene)acetoacetate

Product 1

HCID 3597254Ethyl 4,4,4-trifluoro-2-butynoateYield 83%

Procedure

A mixture of ethyl 4,4,4-trifluoro-2-(triphenylphosphoranylidene)acetoacetate (270 g, 617 mmol) and potassium carbonate (54 g, 490 mmol) is heated from 160° C. to 225° C. in 3 h at 2-3 mbar vacuum. The title compound is distilled and recovered in a cold trap to yield the title compound (85 g, 83%) as a slightly yellow oil. ES/MS m/e 167 (M+1).

Workup

  1. temperatureis heated from 160° C. to 225° C. in 3 h at 2-3 mbar vacuum
  2. distillationThe title compound is distilled
  3. customrecovered in a cold trap

Sources & evidence

ORD record
ord-e508465ae60a4b78a89e9ad6630f01d0
Source dataset
uspto-grants-2012_01
Patent number
US08106077B2

Reaction notes

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