Benzaldehyde → Methyl 4-nitro-5-[(E)-2-phenylethenyl]thiophene-2-carboxylate

HRID 505776Notes

Reaction equation

HRID 505776 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1CCCC1>CO>[N+:11]([C:3]1[CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[S:6][C:2]=1/[CH:1]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 31268Pyrrolidine2×HCID 268679Methyl 5-methyl-4-nitrothiophene-2-carboxylate

Product 1

HCID 11514785Methyl 4-nitro-5-[(E)-2-phenylethenyl]thiophene-2-carboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution (0.33 M) of methyl 5-methyl-4-nitrothiophene-2-carboxylate in MeOH, was treated with benzaldehyde (1.5 eq.). The reaction mixture was heated to reflux and when it became a clear solution a catalytic amount of pyrrolidine (0.01 eq.) was added. After 18 h at reflux additional pyrrolidine (0.01 eq.) was added. The reaction was heated to reflux for 40 h. After cooling down, evaporation of the solvent gave a residue that was purified by flash chromatography on silica gel (1:9 AcOEt/petroleum ether) to afford the title compound (67%) as a solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. additionwas added
  4. additionwas added
  5. temperatureThe reaction was heated
  6. temperatureto reflux for 40 h
  7. temperatureAfter cooling down
  8. customevaporation of the solvent
  9. customgave a residue that
  10. customwas purified by flash chromatography on silica gel (1:9 AcOEt/petroleum ether)

Sources & evidence

ORD record
ord-0dbdf03c2e934233833547dbb1506e68
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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