Sodium Bicarbonate → HCID 67367135, compound

Participants

Reaction Conditions

Reaction Steps

4-(ammonioacetyl)pyridinium dichloride (crude, 100 mg, 0.48 mmol), methyl 2,5-dimethoxytetrahydrofuran-2-carboxylate (99 mg, 0.52 mmol) and sodium acetate (157 mg, 1.9 mmol) were suspended in glacial acetic acid (1.5 mL) and the mixture heated at 100° C. After 4.5 hours the dark mixture was allowed to cool to room temperature and ice (5 g) was added. The mixture was neutralised with solid NaHCO3 and allowed at room temperature. The resulting suspension was diluted with CH2Cl2 (5 mL), filtered and the aqueous layer extracted with CH2Cl2 (3×5 mL). The organic layers were dried (MgSO4), filtered and concentrated in vacuo to yield a brown oil that was purified by flash chromatography (Biotage SP4 (4 g cartridge, gradient hexanes 3 CV, 0-100% EtOAc in hexanes 15 CV, hold for 5 CV) to give methyl 1-[2-oxo-2-(pyridin-4-yl)ethyl]-1H-pyrrole-2-carboxylate (13 mg, yield 11%). ESI-MI m/z [M+H]+ 245.1.

Provenance & Evidence