Acetic acid, azido-, ethyl ester → Ethyl 2-chloro-4H-furo[3,2-b]pyrrole-5-carboxylate

HRID 1368979Notes

Reaction equation

HRID 1368979 reaction equation
[Cl:1][C:2]1[O:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[Na].[CH2:10]([O:12][C:13](=[O:18])[CH2:14][N:15]=[N+]=[N-])[CH3:11]>C(O)C>[CH2:10]([O:12][C:13]([C:14]1[NH:15][C:4]2[CH:3]=[C:2]([Cl:1])[O:6][C:5]=2[CH:7]=1)=[O:18])[CH3:11]

Participants

5

Reactant 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 27696305-Chloro-2-furaldehydeHCID 5360545Sodium

Product 1

HCID 44118832Ethyl 2-chloro-4H-furo[3,2-b]pyrrole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chloro-furan-2-carbaldehyde (Snyder, H. R., Jr.; Seehausen, P. H., J. Heterocycl. Chem., 10: 385-6 (1973)) was annulated according to Procedure H (8 equiv sodium; aldehyde and azido-acetic acid ethyl ester added as ethanol solution (0.9 M of ester); condensation reaction mixture allowed to warm to room temperature, stirred for 1 h, quenched at −40° C., diluted with water, and extracted with ether; acrylate not purified; crude furanopyrrole filtered before concentration).

Workup

  1. customcondensation reaction mixture
  2. customquenched at −40° C.
  3. additiondiluted with water
  4. extractionextracted with ether
  5. customacrylate not purified
  6. filtrationcrude furanopyrrole filtered before concentration)

Sources & evidence

ORD record
ord-7c24c675bbc14fee88507d5278311460
Source dataset
uspto-grants-2003_06
Patent number
US06576653B2

Reaction notes

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