Acetone → Ethyl 2,4-dioxovalerate

HRID 893078Notes

Reaction equation

HRID 893078 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.C(OC(OCC)OCC)C.[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

6

Reactant 4

HCID 180AcetoneHCID 7268Diethyl OxalateHCID 25517Ammonium ChlorideHCID 31214Ethyl orthoformate

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 triethylorthoformate 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-bd23fb219ed94f21b7dddee1a4338d40
Source dataset
uspto-grants-1992_06
Patent number
US05122526

Reaction notes

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