Methanol → 4H,5H,6H-thieno[2,3-c]pyrrol-6-one

HRID 2091563Notes

Reaction equation

HRID 2091563 reaction equation
[NH2:1][CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([O:10]C)=O.C([O-])([O-])=O.[K+].[K+].CO>CCO>[S:5]1[C:4]2[C:8](=[O:10])[NH:1][CH2:2][C:3]=2[CH:7]=[CH:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 53419606Methyl 3-(aminomethyl)thiophene-2-carboxylate

Product 1

HCID 205428054H,5H,6H-thieno[2,3-c]pyrrol-6-oneYield 60.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of methyl 3-(aminomethyl)thiophene-2-carboxylate (4.5 g, 26.3 mmol) and K2CO3 (3.64 g, 26.3 mmol) in 1:1 MeOH:EtOH (600 mL) was heated overnight under reflux. The reaction was concentrated and purified by flash chromatography over silica gel (50-100% EtOAc/hexane) to yield 4H-thieno[2,3-c]pyrrol-6(5H)-one (2.2 g, 60% yield) as a white solid. 1H NMR (400 MHz, METHANOL-d4) δ ppm 7.87 (d, J=4.8 Hz, 1H), 7.17 (d, J=4.8 Hz, 1H), 4.39 (s, 2H); MS (EI) m/z=140.2 [M+1]+.

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction was concentrated
  3. custompurified by flash chromatography over silica gel (50-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-fd8d78be2eda486b922c9541b71cbcbf
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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