Triethylamine → Ethyl p-chlorobenzalpyruvate

HRID 1032043Notes

Reaction equation

HRID 1032043 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8](=[O:12])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH2:15](N(CC)CC)[CH3:16]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8](=[O:12])[C:9]([O:11][CH2:15][CH3:16])=[O:10])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 3674574-(4-Chlorophenyl)-2-oxobut-3-enoic acid

Product 1

HCID 54351366Ethyl p-chlorobenzalpyruvateYield 99%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To the p-chlorobenzalpyruvic acid from step A in wet ethyl acetate was added triethylamine (11.1 g, 0.11 moL) at a rate less than 0.5 mL/min followed by azeotropic removal of water. Ethyl chloroformate (11.9 g, 0.11 moL) was then added at room temperature over a one hour period and the batch aged one hour to effect complete reaction. Workup followed, as in Example 1, to afford ethyl p-chlorobenzalpyruvate in 99% yield.

Workup

  1. customfollowed by azeotropic removal of water
  2. additionEthyl chloroformate (11.9 g, 0.11 moL) was then added at room temperature over a one hour period
  3. customreaction

Sources & evidence

ORD record
ord-175cd20443e9451c9c4ef28cd610ad24
Source dataset
uspto-grants-1990_09
Patent number
US04956490

Reaction notes

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