Hydrochloric Acid → HCID 18507443, compound

Participants

Reaction Conditions

Reaction Steps

Following the method of Turner and Jacks (J. Org Chem. 1989, 54, 4229), to a stirred solution of 11.4 ml (216 mmol) acetonitrile in 50 ml dry THF under argon at −78° C. was added dropwise 95.0 ml (95.0 mmol) lithium bis(trimethylsilyl)amide solution (1 M in THF) and stirring continued for 30 minutes, after which a solution of 7.34 g (43.1 mmol) 5-methoxymethyl-furan-2-carboxylic acid methyl ester in 20 ml THF was added dropwise and stirring continued while the reaction mixture was allowed to warm slowly to −20° C. over 2 hours. The reaction mixture was then cannulated into a rapidly stirred solution of 1M hydrochloric acid at 0° C. The mixtured was extracted twice with ether and the combined organic phases dried over sodium sulfate and concentrated in vacuo. Chromatography (ethyl acetate) afforded 7.73 g (99%) 3-(5-methoxymethyl-furan-2-yl)-3-oxo-propionitrile as an orange crystalline solid. EI-MS m/e (%): 179 (M+, 23), 148 ([M—OCH3]+, 40), 147 ([M—CH3OH]+, 44), 139 ([M—CH2CN]+, 45), 111 ([M—COCH2CN]+, 100).

Provenance & Evidence