4-azido-5-ethoxy-5H-furan-2-one → 4-amino-5-ethoxy-5H-furan-2-one

HRID 2215962Notes

Reaction equation

HRID 2215962 reaction equation
[N:1]([C:4]1[CH:8]([O:9][CH2:10][CH3:11])[O:7][C:6](=[O:12])[CH:5]=1)=[N+]=[N-].[H][H]>[Pd]>[NH2:1][C:4]1[CH:8]([O:9][CH2:10][CH3:11])[O:7][C:6](=[O:12])[CH:5]=1

Participants

4

Reactant 2

HCID 219532314-azido-5-ethoxy-5H-furan-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 219532364-amino-5-ethoxy-5H-furan-2-oneYield 100.9%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 4-azido-5-ethoxy-5H-furan-2-one (0.62 g, 3.67 mmol) and 10% palladium on charcoal (0.31 g) in de-oxygenated ethyl acetate (20 mL) was stirred at 1 atm hydrogen for 24 h. The reaction was filtered (Celite) and evaporated to provide 4-amino-5-ethoxy-5H-furan -2-one (0.53 g, 100% yield) as a yellow oil. 1H-NMR (500 MHz, CDCl3) δ 5.60 (s, 1H), 4.85 (br s, 2H), 4.81 (s, 1H), 3.81 (m, 1H), 3.67 (m, 1H), 1.22 (t, J=7.1 Hz, 3H) ppm.

Workup

  1. filtrationThe reaction was filtered (Celite)
  2. customevaporated

Sources & evidence

ORD record
ord-0f6c5d7ed84b483c949b62a0841e98af
Source dataset
uspto-grants-2006_09
Patent number
US07109357B2

Reaction notes

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