Diethyl Oxalate → HCID 21509105, compound

HRID 268473Notes

Reaction equation

HRID 268473 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:13][C:14]#[N:15])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[C:16](OCC)(=[O:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>[O-]CC.[Na+]>[C:14]([CH:13]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH3:12])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[C:16](=[O:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])#[N:15]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 520318(3,4-Diethoxyphenyl)acetonitrile

Product 1

HCID 21509105HCID 21509105, compound

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

By following the procedures outlined in Examples 1 and 3, 3,4-diethoxyphenylacetonitrile is reacted with diethyl oxalate in alcoholic sodium ethoxide solution to give ethyl 3-cyano-3-(3',4'-diethoxyphenyl)pyruvate. This compound is similarly reacted with 3,4-diethoxyphenylacetonitrile which results in the formation of 2,5-di-(3',4'-diethoxyphenyl)-3,4-dioxoadiponitrile. The latter is refluxed with water, acetic acid and sulfuric acid to give 3,4,3',4'-tetraethoxypulvinic acid which is treated with acetic anhydride to give the corresponding acid lactone.

Sources & evidence

ORD record
ord-f0c7d7cd061c4e91bca454e9d9e5b683
Source dataset
uspto-grants-1976_03
Patent number
US03947580

Reaction notes

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