(3E)-4-Methoxy-3-buten-2-one → Ethyl 1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1662017Notes

Reaction equation

HRID 1662017 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:15])[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:4][CH:3]=1.CO/[CH:18]=[CH:19]/[C:20](=O)[CH3:21].[CH3:23]O[Na]>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:20]([CH3:21])=[CH:19][CH:18]=[C:10]([C:11]([O:13][CH2:14][CH3:23])=[O:12])[C:9]2=[O:15])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 639675(3E)-4-Methoxy-3-buten-2-oneHCID 19901127Methyl 3-(4-fluoroanilino)-3-oxopropanoateHCID 178418582HCID 178418582, compound

Product 1

HCID 66767307Ethyl 1-(4-fluorophenyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylateYield 16%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 3-(4-fluorophenylamino)-3-oxopropanoate(10.1 g, 48 mmol) in EtOH (100 mL) is added trans-4-methoxy-3-buten-2-one (5.7 g, 57 mmol) and CH3ONa (3.1 g, 57 mmol). The mixture is heated at reflux overnight and then concentrated. The residue is purified by silica gel column chromatography eluting with PE:EtOAC (from 5:1 to 2:1) to give the product (2.1 g, 16% yield). MS (m/z): 276.1 (M+H).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated
  4. customThe residue is purified by silica gel column chromatography
  5. washeluting with PE

Sources & evidence

ORD record
ord-de165dc2c78f4887a68a842b4f8c95f8
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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