Diethyl Oxalate → HCID 359722, compound

HRID 267757Notes

Reaction equation

HRID 267757 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].CC[O-].[Na+].[Na]>C(O)(=O)C.O>[C:9]([CH:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10]

Participants

7

Reactant 4

HCID 7268Diethyl OxalateHCID 2415824-Chlorobenzyl cyanideHCID 2723922Sodium ethoxideHCID 5360545Sodium

Product 1

HCID 359722HCID 359722, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

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

Workup

  1. additionA mixture of 45.3 g
  2. customThe cooled reaction mixture
  3. additionis diluted with 700 ml
  4. temperaturecooled to ice bath temperature
  5. customThe resulting solid is recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-a5604386597044bb9bfb8a3b1f31441f
Source dataset
uspto-grants-1976_03
Patent number
US03944571

Reaction notes

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