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

HRID 2184703Notes

Reaction equation

HRID 2184703 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=O)[O:5][CH:6]=1.[O-:9][CH2:10][CH3:11].[NH4+:12].[Cl-].[C:14]([O-:18])(=O)[CH:15]=C>O.CCOCC.C(O)C>[CH2:10]([O:9][C:14]([C:15]1[NH:12][C:3]2[C:2]([Br:1])=[CH:6][O:5][C:4]=2[CH:7]=1)=[O:18])[CH3:11]

Participants

8

Reactant 4

HCID 25188Acrylate2×HCID 25517Ammonium ChlorideHCID 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 add 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-59a91402f3c74ee2bcd3fd8a05d103ab
Source dataset
uspto-grants-2002_06
Patent number
US06399601B1

Reaction notes

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