Pyridine → 2,2,2-Trichloroethyl 2-oxopropanoate

HRID 867219Notes

Reaction equation

HRID 867219 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[O:3].ClC(O[CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])=O.N1C=CC=CC=1>O1CCCC1>[C:1]([O:6][CH2:11][C:12]([Cl:15])([Cl:14])[Cl:13])(=[O:5])[C:2]([CH3:4])=[O:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1060Pyruvic AcidHCID 870632,2,2-Trichloroethyl chloroformate

Product 1

HCID 129644372,2,2-Trichloroethyl 2-oxopropanoateYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.3 g (37.5 mmole) of pyruvic acid and 7.9 g (37.5 mmole) of trichloroethyl chloroformate in 20 ml of dry tetrahydrofuran at 0° is added dropwise 0.6 ml of pyridine. After stirring for 2 hrs. at room temperature, the mixture is concentrated in vacuum, diluted with water and extracted with ethyl acetate. The extract is washed with 5% HCl, dried over MgSO4, evaporated and distilled in vacuum to give 4.0 g (50%) trichloroethyl pyruvate, bp 75°-82° (17 mm).

Workup

  1. concentrationat room temperature, the mixture is concentrated in vacuum
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washThe extract is washed with 5% HCl
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-5d1d7aa5dcab47559aeaa62b3b52ebc9
Source dataset
uspto-grants-1978_07
Patent number
US04103086

Reaction notes

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