Acetic Acid → methyl 4H-thieno(3,2-b)pyrrole-2-carboxylate

HRID 1442540Notes

Reaction equation

HRID 1442540 reaction equation
CN(C)/[CH:3]=[CH:4]/[C:5]1[S:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][C:6]=1[N+:14]([O-])=O.C(O)(=O)C>O1CCCC1.[Pd]>[S:9]1[C:5]2[CH:4]=[CH:3][NH:14][C:6]=2[CH:7]=[C:8]1[C:10]([O:12][CH3:13])=[O:11]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 12110978methyl (E)-5-(2-dimethylaminovinyl)-4-nitrothiophene-2-carboxylate

Product 1

HCID 12110979methyl 4H-thieno(3,2-b)pyrrole-2-carboxylateYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl (E)-5-(2-dimethylaminovinyl)-4-nitrothiophene-2-carboxylate (20 g, 78 mmol), 5% palladium/carbon (2 g) and acetic acid (20 ml) in tetrahydrofuran (300 ml) was stirred under hydrogen atmosphere (3.5 atm) at room temperature for 16 hr. The reaction mixture was filtered through celite and concentrated under reduced pressure. Diethyl ether (300 ml) was added to the residue. The mixture was washed successively with 1N hydrochloric acid (100 ml×2), water (100 ml), saturated aqueous sodium hydrogen carbonate solution (100 ml×2) and saturated brine (100 ml), and dried over magnesium sulfate. Filtration and concentration under reduced pressure gave methyl 4H-thieno[3,2-b]pyrrole-2-carboxylate (12 g, yield 87%).

Workup

  1. filtrationThe reaction mixture was filtered through celite and
  2. concentrationconcentrated under reduced pressure
  3. additionDiethyl ether (300 ml) was added to the residue
  4. washThe mixture was washed successively with 1N hydrochloric acid (100 ml×2), water (100 ml), saturated aqueous sodium hydrogen carbonate solution (100 ml×2) and saturated brine (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationFiltration and concentration under reduced pressure

Sources & evidence

ORD record
ord-239187d8baf84a19bab1c1aad3a75b0c
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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