Formamide → 2-Methyl-2-(5-fluorobenzofur-7-yl)propionamide

HRID 1824967Notes

Reaction equation

HRID 1824967 reaction equation
[CH3:1][C:2]([C:9]1[C:17]2[O:16][CH:15]=[CH:14][C:13]=2[CH:12]=[C:11]([F:18])[CH:10]=1)([CH3:8])[C:3](OCC)=[O:4].C([NH2:21])=O.C[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]([C:9]1[C:17]2[O:16][CH:15]=[CH:14][C:13]=2[CH:12]=[C:11]([F:18])[CH:10]=1)([CH3:8])[C:3]([NH2:21])=[O:4]

Participants

6

Reactant 3

HCID 713FormamideHCID 10942334Sodium MethoxideHCID 22144774HCID 22144774, compound

Product 1

HCID 221449242-Methyl-2-(5-fluorobenzofur-7-yl)propionamideYield 43.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 0.156 gm (0.62 mMol) ethyl 2-methyl-2-(5-fluorobenzofur-7-yl)propionate, 0.095 gm (2.12 mMol) formamide, and 0.44 mL (0.44 mMol) sodium methoxide (1.0 M in methanol) in 3 mL dimethylformamide was heated at 100° C. for 45 minutes. The reaction mixture was diluted with ethyl acetate and the organics washed sequentially with water and saturated aqueous sodium chloride. The organics were then concentrated under reduced pressure and the residue subjected to silica gel chromatography, eluting with 2:1 hexane:ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 0.060 gm (25%) of the desired compound.

Workup

  1. washthe organics washed sequentially with water and saturated aqueous sodium chloride
  2. concentrationThe organics were then concentrated under reduced pressure
  3. washeluting with 2:1 hexane
  4. additionFractions containing product
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7f7c4803cc5e45368f5ee0a1cae18222
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

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