Acetic Acid → Methyl furan-2-carboximidate

HRID 1588561Notes

Reaction equation

HRID 1588561 reaction equation
[C:1]([C:3]1[O:4][CH:5]=[CH:6][CH:7]=1)#[N:2].C[O-].[Na+].[C:11](O)(=[O:13])C>CO>[O:4]1[CH:5]=[CH:6][CH:7]=[C:3]1[C:1](=[NH:2])[O:13][CH3:11]

Participants

5

Procedure

2-Cyanofuran (4.50 9, 48.3 mmol) was dissolved in methanol (25 ml), and sodium methoxide (130 mg, 2.4 mmol) was added under ice-cooling. The mixture was stirred while the temperature is slowly raised up to room temperature for 2 hours. After the reaction was completed, acetic acid (0.16 g, 2.6 mmol) was added to neutralize the reaction solution, and the solution was concentrated under reduced pressure. Diethyl ether (100 ml) was added to the concentrated residue, and insolubles were removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product of methyl 2-furancarboximidate (6.0 g) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. concentrationthe solution was concentrated under reduced pressure
  3. additionDiethyl ether (100 ml) was added to the concentrated residue, and insolubles
  4. customwere removed by filtration
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-88bd24d98cf8497f8f116daf68878165
Source dataset
uspto-grants-1993_06
Patent number
US05223508

Reaction notes

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