Sodium Azide → 4-azido-5-ethoxy-5H-furan-2-one

HRID 2215961Notes

Reaction equation

HRID 2215961 reaction equation
Br[C:2]1[CH:6]([O:7][CH2:8][CH3:9])[O:5][C:4](=[O:10])[CH:3]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C)C=O.C(OCC)(=O)C>[N:11]([C:2]1[CH:6]([O:7][CH2:8][CH3:9])[O:5][C:4](=[O:10])[CH:3]=1)=[N+:12]=[N-:13]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 124232244-Bromo-5-ethoxy-2,5-dihydrofuran-2-one

Product 1

HCID 219532314-azido-5-ethoxy-5H-furan-2-oneYield 62%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-bromo-5-ethoxy-5H-furan-2-one (2.07 g, 10.0 mmol) and sodium azide (0.66 g, 10.2 mmol) in dimethylformamide (10 mL) was stirred at room temperature under nitrogen for 24 h. The reaction was diluted with ethyl acetate, was washed with 0° C. water and with brine, was dried over sodium sulfate, and was evaporated. Purification by flash chromatography (SiO2) eluted with 1:9 ethyl acetate:hexanes afforded 4-azido-5-ethoxy-5H-furan-2-one (1.04 g, 62% yield) as a pale yellow oil. 1H-NMR (500 MHz, CDCl3) δ 5.83 (s, 1H), 5.63 (s, 1H), 3.99 (m, 1H), 3.88 (m, 1H), 1.35 (t, J=7.1 Hz, 3H) ppm.

Workup

  1. washwas washed with 0° C. water
  2. dry with materialwith brine, was dried over sodium sulfate
  3. customwas evaporated
  4. customPurification by flash chromatography (SiO2)
  5. washeluted with 1:9 ethyl acetate

Sources & evidence

ORD record
ord-c8c930bde6a747949ea93dfb931ee945
Source dataset
uspto-grants-2006_09
Patent number
US07109357B2

Reaction notes

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