Acetone → Ethyl 2,4-dioxovalerate

HRID 330061

Reaction equation

HRID 330061 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-f6734b59d09746dda665bd65287785b5
Source dataset
uspto-grants-1990_01
Patent number
US04894456

Linked notes

Loading…