Acrylate → Ethyl 3-bromo-4H-furo[3,2-b]pyrrole-5-carboxylate

HRID 1368988Notes

Reaction equation

HRID 1368988 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[O:5][CH:6]=1.[CH2:9]([O:11][C:12](=[O:17])[CH2:13][N:14]=[N+]=[N-])[CH3:10].[O-]CC.[NH4+].[Cl-].C([O-])(=O)C=C>O.CCOCC.C(O)C>[CH2:9]([O:11][C:12]([C:13]1[NH:14][C:3]2[C:2]([Br:1])=[CH:6][O:5][C:4]=2[CH:7]=1)=[O:17])[CH3:10]

Participants

9

Reactant 5

HCID 25188Acrylate2×HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 1194401-Hydroxyethyl radicalHCID 27570104-Bromo-2-furaldehyde

Product 1

HCID 59648581Ethyl 3-bromo-4H-furo[3,2-b]pyrrole-5-carboxylate

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

4-Bromo-2-furaldehyde was annulated according to Procedure H (aldehyde and azido-acetic acid ethyl ester added as ethanol solution (1 M of ester) to −20° C. ethoxide solution; −20° C. 35 min, −5° C. 1.5 h, 5° C. 15 min; reaction poured into cold saturated aqueous NH4Cl; after ether extraction, acrylate organic phase washed with water until aqueous phase was neutral; 0.5 M solution of crude acrylate heated).

Sources & evidence

ORD record
ord-5b9f546e5c0d48e2892a1f0521a9f459
Source dataset
uspto-grants-2003_06
Patent number
US06576653B2

Reaction notes

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