Methyl 4-nitro-5-[(E)-2-phenylethenyl]thiophene-2-carboxylate → methyl 5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 505777Notes

Reaction equation

HRID 505777 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[S:7][C:8]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O-])=O>P(OCC)(OCC)OCC>[C:11]1([C:10]2[NH:1][C:4]3[CH:5]=[C:6]([C:17]([O:19][CH3:20])=[O:18])[S:7][C:8]=3[CH:9]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 11514785Methyl 4-nitro-5-[(E)-2-phenylethenyl]thiophene-2-carboxylate

Product 1

HCID 11492603methyl 5-phenyl-4H-thieno[3,2-b]pyrrole-2-carboxylateYield 32%

Reagents, catalysts & solvents 1

HCID 31215Triethyl phosphiteSolvent

Procedure

A solution (1 M) of methyl 4-nitro-5-[(E)-2-phenylethenyl]thiophene-2-carboxylate in triethyl phosphite was heated to reflux for 28 h. After cooling down a part of the solvent was evaporated under high vacuum (2 mbar, water bath 60° C.) then the residue was purified by flash chromatography on silica gel (1:4 acetone/toluene) to afford the title compound (32%) as a solid.

Workup

  1. temperatureto reflux for 28 h
  2. temperatureAfter cooling down a part of the solvent
  3. customwas evaporated under high vacuum (2 mbar, water bath 60° C.)
  4. customthe residue was purified by flash chromatography on silica gel (1:4 acetone/toluene)

Sources & evidence

ORD record
ord-181af2c72d4b4190811eda0deb196a4e
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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