Diethyl Oxalate → Ethyl 3-cyano-3-phenylpyruvate

HRID 1085837Notes

Reaction equation

HRID 1085837 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[O-].[Na+].[C:14](OCC)(=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>>[C:2]1([CH:1]([C:8]#[N:9])[C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7268Diethyl OxalateHCID 8794PhenylacetonitrileHCID 2723922Sodium ethoxide

Product 1

HCID 22845Ethyl 3-cyano-3-phenylpyruvateYield 90%

Procedure

Reaction of benzyl cyanide, sodium ethylate and diethyl oxalate according to the method described in Org. Synth. Coll. Vol. II (1943) 287 and Chem. Ber. 107 (1974) 2794-2795 in alcohol, acidification with conc. (37%) hydrochloric acid to pH 2 and subsequent recrystallization of the separated precipitate from ethanol yielded ethyl phenylcyanopyruvate in 90% yield as yellow crystals, melting point 127°-128°.

Workup

  1. custom107 (1974) 2794-2795 in alcohol, acidification with conc. (37%) hydrochloric acid to pH 2 and subsequent recrystallization of the separated precipitate from ethanol

Sources & evidence

ORD record
ord-24997745654c4a98838fd6991246e5ff
Source dataset
uspto-grants-1991_04
Patent number
US05011849

Reaction notes

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