Diethyl Oxalate → HCID 57691411, compound

HRID 548596Notes

Reaction equation

HRID 548596 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][C:15]#[N:16])[C:4]([CH3:7])=[CH:5][CH:6]=1.[C:17](OCC)(=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19].CC(C)([O-])C.[Na+]>C(O)C>[C:15]([CH:14]([C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N:3]1[C:2]([CH3:1])=[CH:6][CH:5]=[C:4]1[CH3:7])[C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])#[N:16]

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 23676156Sodium t-butoxideHCID 576914142-(2,5-Dimethylpyrrol-1-yl)phenylacetonitrile

Product 1

HCID 57691411HCID 57691411, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

2-(2,5-Dimethylpyrrol-1-yl)phenylacetonitrile (15 mmol) and diethyl oxalate (4.38 g, 30 mml) were sequentially added neat washing with ethanol (15 mL) to a solution of sodium tert-butoxide (1.73 g, 18 mmol) in ethanol (15 mL). The reaction mixture was heated at reflux under a nitrogen atmosphere for 4.5 hours to provide a solution of ethyl 3-cyano-3-[2-(2,5-dimethylpyrrol-1-yl)phenyl]-2-oxopropionate in ethanol.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under a nitrogen atmosphere for 4.5 hours

Sources & evidence

ORD record
ord-c6f812c8a7064f3480daec585ca84fab
Source dataset
uspto-grants-2011_05
Patent number
US07943610B2

Reaction notes

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