4-Chlorobenzaldehyde → methyl 5-[(E)-2-(4-chlorophenyl)vinyl]4-nitrothiophene-2-carboxylate

HRID 505792Notes

Reaction equation

HRID 505792 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].[Cl:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.N1CCCC1>CO>[Cl:14][C:15]1[CH:22]=[CH:21][C:18](/[CH:19]=[CH:1]/[C:2]2[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][C:3]=2[N+:11]([O-:13])=[O:12])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 77264-ChlorobenzaldehydeHCID 31268PyrrolidineHCID 268679Methyl 5-methyl-4-nitrothiophene-2-carboxylate

Product 1

HCID 68471094methyl 5-[(E)-2-(4-chlorophenyl)vinyl]4-nitrothiophene-2-carboxylateYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution (1.74 M) of methyl 5-methyl-4-nitrothiophene-2-carboxylate (prepared as described in example 1, step 1) in MeOH, was treated with 4-chlorobenzaldehyde (1.5 eq.). The reaction mixture was heated to reflux and when it became a clear solution, a catalytic amount of pyrrolidine (0.10 eq.) was added. The reaction mixture was heated to reflux overnight. After cooling down, evaporation of the solvent gave a residue that was triturated with petroleum ether/Et2O and filtered to afford the title compound title compound (67%) as a solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureto reflux overnight
  5. temperatureAfter cooling down
  6. customevaporation of the solvent
  7. customgave a residue that
  8. customwas triturated with petroleum ether/Et2O
  9. filtrationfiltered

Sources & evidence

ORD record
ord-689230cc1d6842b08e211d86aa259735
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

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