Water → ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylate

HRID 1713039Notes

Reaction equation

HRID 1713039 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([N:12]=[N+]=[N-])=[CH:6][C:7]1[S:8][CH:9]=[CH:10][CH:11]=1)[CH3:2].O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[NH:12][C:11]2[CH:10]=[CH:9][S:8][C:7]=2[CH:6]=1)=[O:15])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 54362140Ethyl 2-azido-3-(2-thienyl)propenoate2×

Product 1

HCID 292163ethyl 4H-thieno[3,2-b]pyrrole-5-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The resulting azide, 2-azido-3-thiophen-2-yl-acrylic acid ethyl ester (650 mg, 2.88 mmol) was dissolved in toluene (40 ml) and the solution was refluxed for 2 hours. The solution was thereafter cooled, and water (80 ml) was added. After separation of the phases the aqueous phase was extracted with ethyl acetate (3×20 ml), the combined organic phase was dried over Na2SO4 and the organic solvents were evaporated under reduced pressure. The crude product was purified by silica gel flash chromatography to give 450 mg of pure 4H-thieno[3,2-b]pyrrole-5-carboxylic acid ethyl ester (80% yield).

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. temperatureThe solution was thereafter cooled
  3. customAfter separation of the phases the aqueous phase
  4. extractionwas extracted with ethyl acetate (3×20 ml)
  5. dry with materialthe combined organic phase was dried over Na2SO4
  6. customthe organic solvents were evaporated under reduced pressure
  7. customThe crude product was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-5ec4183f2c9342808eaca87fe02f2cba
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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