Diethyl Oxalate → Ethyl 3-cyano-2-oxo-4-phenylbutanoate

HRID 485692Notes

Reaction equation

HRID 485692 reaction equation
[Na].[C:2]([O:9][CH2:10][CH3:11])(=[O:8])[C:3]([O:5]CC)=O.[C:12](#[N:21])[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[C:12]([CH:13]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3](=[O:5])[C:2]([O:9][CH2:10][CH3:11])=[O:8])#[N:21]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 12581BenzenepropanenitrileHCID 5360545Sodium

Product 1

HCID 13491334Ethyl 3-cyano-2-oxo-4-phenylbutanoateYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

920 mg sodium (40 mmole) is dissolved in 45 ml ethanol and to the ice-bath cooled solution is added 4.66 g diethyl oxalate (31.9 mmole) and 4.17 g hydrocinnamonitrile (31.9 mmole). The mixture is stirred at room temperature for 1 hour, under reflux for 3 hours, and then allowed to stand at room temperature overnight. Evaporation, acidification of the residue, and extraction with methylene chloride affords ethyl 3-cyano-2-oxo-4-phenylbutanoate in 38% yield. The compound crystallizes from petroleum ether in colorless needles; m.p. 80°-83° C.

Workup

  1. temperaturecooled solution
  2. temperatureunder reflux for 3 hours
  3. waitto stand at room temperature overnight
  4. customEvaporation, acidification of the residue, and extraction with methylene chloride

Sources & evidence

ORD record
ord-9f9e9bca059942f389eddd98ba332b47
Source dataset
uspto-grants-1985_08
Patent number
US04537902

Reaction notes

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