Ethyl 2-azido-3-(2-thienyl)propenoate → ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate
Reaction equation
[N:1]([C:4](=[CH:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-]>C1(C)C(C)=CC=CC=1>[S:12]1[C:11]2[CH:10]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[NH:1][C:15]=2[CH:14]=[CH:13]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of ethyl 2-azido-3-(2-thienyl)propenoate (0.45 g) in xylene (10 ml) was heated at reflux for 30 minutes, concentrated in vacuo and the residue purified by column chromatography using isohexane-15% ethyl acetate as eluent to give the product as a pale yellow solid (0.26 g, 66%), NMR d(CDCl3) 1.40 (3H, t), 4.39 (2H, q), 6.98 (1H, d), 7.18 (1H, s), 7.35 (1H, d), 9.30 (1H, bs) M/z (−) 194 (M-H+), 166.
Workup
- temperatureat reflux for 30 minutes
- concentrationconcentrated in vacuo
- customthe residue purified by column chromatography
Sources & evidence
- ORD record
- ord-a39e25ed253746e2a300e0fa1313e708
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479527B1
Reaction notes
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