Ethanol → 2-bromo-4H-furo[3,2-b]pyrrole-5-carboxylic acid

HRID 2184686Notes

Reaction equation

HRID 2184686 reaction equation
C(OC([C:6]1([Br:14])[O:13][C:12]2[CH:11]=[CH:10][NH:9][C:8]=2[CH2:7]1)=O)C.[OH-:15].[Na+].[CH2:17]([OH:19])C>>[Br:14][C:6]1[O:13][C:12]2[CH:11]=[C:10]([C:17]([OH:19])=[O:15])[NH:9][C:8]=2[CH:7]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 70159654HCID 70159654, compound

Product 1

HCID 225565062-bromo-4H-furo[3,2-b]pyrrole-5-carboxylic acid

Procedure

2-Bromo-4H-furo[3,2-b]pyrrole-carboxylic acid ethyl ester (Krutosikova, A.; Kovac, J.; Dandarova, M.; Lesko, J.; Ferik, S., Collect Czech. Chem. Commun., 46: 2564-2573 (1981)) was hydrolyzed according to Procedure E (4 equiv 2 N NaOH, ethanol; reflux 5h, room temperature overnight; after concentration to remove ethanol, residue partitioned between ethyl acetate and 2 N HCl; combined organic phases dried over Na2SO4; no purification). 1H NMR (DMSO-d6) δ 12.47 (br s, 1H), 11.67 (s, 1H), 6.76 (d, J=0.8 Hz, 1H), 6.67 (t, J=0.8Hz, 1H).

Workup

  1. custom, Collect Czech
  2. concentrationafter concentration
  3. customto remove ethanol, residue
  4. custompartitioned between ethyl acetate and 2 N HCl
  5. dry with materialcombined organic phases dried over Na2SO4
  6. customno purification)

Sources & evidence

ORD record
ord-1a193dc2e51548a1b907fbce7191e824
Source dataset
uspto-grants-2002_06
Patent number
US06399601B1

Reaction notes

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