Acetone → Ethyl 2,4-dioxovalerate

HRID 2379710Notes

Reaction equation

HRID 2379710 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-782ebd49740b43a8bea963f82ccef9e2
Source dataset
uspto-grants-1994_11
Patent number
US05364858

Reaction notes

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