Diethyl Oxalate → HCID 359722, compound

HRID 1287531Notes

Reaction equation

HRID 1287531 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[C:11](OCC)(=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13].[O-]CC.[Na+].[Na].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:9]#[N:10])[C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 7268Diethyl OxalateHCID 2415824-Chlorobenzyl cyanideHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 359722HCID 359722, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 45.3 g. (0.31 mol.) of p-chlorophenylacetonitrile and 107 g. (0.72 mol., 99 ml.) of diethyl oxalate in an alcoholic sodium ethoxide solution [prepared by dissolving 7.13 g. (0.31 g.-atom) of sodium in 120 ml. of absolute ethanol] was refluxed with stirring for 2 hours. The cooled reaction mixture was diluted with 700 ml. of water, acidified with acetic and cooled to ice bath temperature. The resulting solid was collected and recrystallized from aqueous methanol to give ethyl 3-(p-chlorophenyl)-3-cyanopyruvate, m.p. 134°-135°.

Workup

  1. additionA mixture of 45.3 g
  2. customThe cooled reaction mixture
  3. additionwas diluted with 700 ml
  4. temperaturecooled to ice bath temperature
  5. customThe resulting solid was collected
  6. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-e20668dd209845a3bc0d553ab68f46b2
Source dataset
uspto-grants-1976_10
Patent number
US03984559

Reaction notes

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