Pyrrolidine → HCID 58679079, compound

HRID 1442527Notes

Reaction equation

HRID 1442527 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([O:12][CH3:13])=[O:11])[S:7][C:8]=1[CH3:9])([O-:3])=[O:2].[CH2:14]([O:21][C:22]1[CH:29]=[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]=[CH:26][C:23]=1[CH:24]=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1CCCC1>C(O)C>[CH2:14]([O:21][C:22]1[CH:29]=[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:27]=[CH:26][C:23]=1/[CH:24]=[CH:9]/[C:8]1[S:7][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 268679Methyl 5-methyl-4-nitrothiophene-2-carboxylateHCID 18090802,4-Bis(benzyloxy)benzaldehyde

Product 1

HCID 58679079HCID 58679079, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl 4-nitro-5-methylthiophene-2-carboxylate (1.50 g, 7.46 mmol) in ethanol (7.5 ml) were added 2,4-bisbenzyloxybenzaldehyde (2.49 g, 7.83 mmol) and pyrrolidine (0.65 ml, 7.83 mmol). After stirring for 1 hr with heating under reflux, the reaction mixture was allowed to cool to room temperature. The precipitated solid was collected by filtration. The solid was washed with ethanol (3 ml×3), and dried under reduced pressure to give methyl (E)-5-[2-(2,4-bisbenzyloxyphenyl)vinyl]-4-nitrothiophene-2-carboxylate (3.08 g, yield 82%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. filtrationThe precipitated solid was collected by filtration
  4. washThe solid was washed with ethanol (3 ml×3)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-cdc63fbfca894cc4bccaf77020631e05
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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