Trifluoroacetic acid → Diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate

HRID 1090817

Reaktionsgleichung

[C:1]([C:9]1[NH:13][C:12]([C:14](OC(=O)C)([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([C:9]1[NH:13][C:12]([CH:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 40 °C

Versuchsvorschrift

To a solution of diethyl (5-benzoylpyrrol-2-yl)-acetoxymethanedicarboxylate (142 mg, 0.367 mmol) and triethylsilane (102 mg, 0.440 mmol) in methylene chloride (10 mL) was added trifluoroacetic acid (84 mg, 0.734 mmol). The reaction mixture was stirred at 40° C. for 24 hours. Additional triethyl silane (51 mg, 0.220 mmol) and trifluoroacetic acid (84 mg, 0.734 mmol) was added. The reaction mixture was stirred at 40° C. for an additional 24 hours. The mixture was cooled to room temperature, washed with cold 10% aqueous sodium hydroxide and saturated aqueous sodium chloride, and concentrated under reduced pressure. The residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (87:13) to provide 60 mg (50%) of diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate.

Aufarbeitung

stirringThe reaction mixture was stirred at 40° C. for an additional 24 hours
temperatureThe mixture was cooled to room temperature
washwashed with cold 10% aqueous sodium hydroxide and saturated aqueous sodium chloride
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (87:13)

Quellen und Nachweise

ORD-Eintrag: ord-45462bd281c8487caa0b0a8ec0a9d15f
Quelldatensatz: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05082950

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