Tetrabutylammonium Fluoride → ethyl 4H-thieno[3,2-b]pyrrole-2-carboxylate

HRID 505805Notes

Reaction equation

HRID 505805 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[S:12][C:13]=1[C:14]#[C:15][Si](C)(C)C)=O)(C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[S:12]1[C:13]2[CH:14]=[CH:15][NH:8][C:9]=2[CH:10]=[C:11]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 25258327HCID 25258327, compound

Product 1

HCID 25258328ethyl 4H-thieno[3,2-b]pyrrole-2-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution (0.3 M) of ethyl 4-[(tert-butoxycarbonyl)amino]-5-[(trimethylsilyl)ethynyl]thiophene-2-carboxylate in THF was treated with n-Bu4NF (2 eq.). The mixture was irradiated in a microwave apparatus at 120° C. for 20 min. Evaporation of the solvent gave a residue that was purified by flash chromatography on silica gel (1:3 AcOEt/petroleum ether) to afford the title compound (94%) as a solid.

Workup

  1. customThe mixture was irradiated in a microwave apparatus at 120° C. for 20 min
  2. customEvaporation of the solvent
  3. customgave a residue that
  4. customwas purified by flash chromatography on silica gel (1:3 AcOEt/petroleum ether)

Sources & evidence

ORD record
ord-1d942b4bd6d447e7a10714ec2a4312d3
Source dataset
uspto-grants-2010_08
Patent number
US07781431B2

Reaction notes

Loading…