methyl 5-cyanofuran-2-carboxylate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of the ester from step 1 (0.098 g, 0.652 mmol), in ethanol (2.5 ml) at 0° C. was treated with sodium borohydride (0.11 g, 2.936 mmol) and the reaction was stirred for 2 hrs. Saturated NH4Cl solution (1 ml) was added and the aqueous extracted with diethylether. The combined extracts were dried (MgSO4) and evaporated in vacuo. The residue was chromatographed (silica gel, diethylether) to afford the title compound. the aqueous extracted with diethylether The combined extracts were dried (MgSO4) evaporated in vacuo The residue was chromatographed (silica gel, diethylether)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of the ester from step 1 (0.098 g, 0.652 mmol), in ethanol (2.5 ml) at 0° C. was treated with sodium borohydride (0.11 g, 2.936 mmol) and the reaction was stirred for 2 hrs. Saturated NH4Cl solution (1 ml) was added and the aqueous extracted with diethylether. The combined extracts were dried (MgSO4) and evaporated in vacuo. The residue was chromatographed (silica gel, diethylether) to afford the title compound. the aqueous extracted with diethylether The combined extracts were dried (MgSO4) evaporated in vacuo The residue was chromatographed (silica gel, diethylether)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To 1,67 g (41.7 mmol, 60% dispersion in mineral oil) sodium hydride in a 2-necked flask fitted with a reflux condenser was added dropwise 150 ml THF and the mixture was then heated to reflux. A solution of 1.0 ml (208 mmol) acetonitrile and 6.30 g (41.7 mmol) 5-cyano-furan-2-carboxylic acid methyl ester in 100 ml dry THF was added dropwise and the reaction mixture heated at reflux for 4 hours. The reaction mixture was then cannulated into a rapidly stirred solution of 1M hydrochloric acid at 0° C. The mixture was extracted three times with ethyl acetate and the combined organic phases dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate/hexane 1/1) afforded 2.90 g (43%) 5-cyanoacetyl-furan-2-carbonitrile as an orange oil. EI-MS m/e (%): 160 (M+, 19), 120 ([M—CH2CN]+, 100). the mixture was then heated to reflux the reaction mixture heated at reflux for 4 hours The mixture was extracted three times with ethyl acetate the combined organic phases dried over sodium sulfate concentrated in vacuo