Acetone → Ethyl 2,4-dioxovalerate

HRID 1609472Notes

Reaction equation

HRID 1609472 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-096890358e644b6497b847051302165b
Source dataset
uspto-grants-1995_03
Patent number
US05401747

Reaction notes

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