Diethyl Oxalate → HCID 19768834, compound

HRID 268472Notes

Reaction equation

HRID 268472 reaction equation
[F: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+]>[C:9]([CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10]

Participants

4

Reactant 2

HCID 7268Diethyl OxalateHCID 68016Benzeneacetonitrile, 4-fluoro-

Product 1

HCID 19768834HCID 19768834, compound

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

By employing the procedures described in Example 1, p-fluorophenylacetonitrile is reacted with diethyl oxalate in alcoholic sodium ethoxide to give ethyl 3-cyano-3-(p-fluoro-phenyl)pyruvate. The latter is reacted with phenylacetonitrile and subsequent synthetic steps yield 4-fluoropulvinic acid lactone. The lactone ring is opened with 2-aminothiazole as described above to give 4-fluoro-N-(2-thiazolyl)pulvinic acid amide.

Sources & evidence

ORD record
ord-bf493dbddee34045985654fe3cbc796a
Source dataset
uspto-grants-1976_03
Patent number
US03947580

Reaction notes

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