Acetone → Ethyl 2,4-dioxovalerate

HRID 703251Notes

Reaction equation

HRID 703251 reaction equation
[CH3:1][C:2]([CH3:4])=[O:3].[C:5]([O:12][CH2:13][CH3:14])(=[O:11])[C:6]([O:8]CC)=O.[Cl-].[NH4+]>C(O)C>[CH3:14][CH2:13][O:12][C:5]([C:6]([CH2:1][C:2]([CH3:4])=[O:3])=[O:8])=[O:11]

Participants

5

Reactant 3

HCID 180AcetoneHCID 7268Diethyl OxalateHCID 25517Ammonium Chloride

Product 1

HCID 69208Ethyl 2,4-dioxovalerate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl acetopyruvate was prepared from acetone and diethyl oxalate as described in Org. Synthesis, Coll. Vol. 1, 238 (1958). Further reaction with triethylorthofcrmate and ammonium chloride in ethanol. afforded the known enol ether 1. See L. Claisen, Chem. Ber., 40, 3903 (1907).

Workup

  1. customSynthesis, Coll

Sources & evidence

ORD record
ord-2e62f15aefd442e2bd58ec4ec8d7256c
Source dataset
uspto-grants-1991_01
Patent number
US04981968

Reaction notes

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