Trimethylsilyldiazomethane → methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate

HRID 1363266

Reaktionsgleichung

[S:1]1[C:8]2[CH:7]=[C:6]([C:9]([OH:11])=[O:10])[NH:5][C:4]=2[CH:3]=[CH:2]1.[CH3:12][Si](C=[N+]=[N-])(C)C>CO>[S:1]1[C:8]2[CH:7]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[NH:5][C:4]=2[CH:3]=[CH:2]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

4H-thieno[3,2-b]pyrrole-5-carboxylic acid (3.0 g, 17.9 mmol) was dissolved in anhydrous MeOH (50.0 mL) and cooled to 0° C. A solution (45.0 mL, 2 M in hexanes) of trimethylsilyldiazomethane (45 mL) was added in portions and the yellow color of the TMSCH2N2 remained. Stirring was continued for 10 min and then the excess TMSCH2N2 was quenched with acetic acid (5.0 mL). The solvent was removed with N2 stream, and the residue was chromatographed over silica gel (5%-40%, 30 min, EtOAc in heptane) to give methyl 4H-thieno[3,2-b]pyrrole-5-carboxylate (2.8 g, 86% yield). 1H NMR (400 MHz, CD3Cl) δ ppm 3.90 (s, 3H) 6.95 (dd, J=5.32, 0.78 Hz, 1H) 7.13 (dd, J=1.88, 0.76 Hz, 1H) 7.33 (d, J=5.37 Hz, 1H) 9.02 (br. s, 1H).

Aufarbeitung

customthe excess TMSCH2N2 was quenched with acetic acid (5.0 mL)
customThe solvent was removed with N2 stream
customthe residue was chromatographed over silica gel (5%-40%, 30 min, EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag: ord-639a84915ca14e369ce8dc4aaed361e0
Quelldatensatz: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07884124B2

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