Dimethyl Sulfoxide → HCID 86583759, compound

Participants

Reaction Steps

Following the method of Rudorf and Augustin (Phosphorus and Sulfur 1981, 9, 329), a solution of 1.00 g (5.58 mmol) 3-(5-methoxymethyl-furan-2-yl)-3-oxo-propionitrile in 15 ml dry DMSO was added dropwise to a stirred suspension of 487 mg (11.2 mmol, 60% dispersion in mineral oil) sodium hydride in 15 ml DMSO under argon at room temperature. 0.34 ml (5.58 mmol) carbon disulfide was then added dropwise, with external water bath cooling, and stirring continued for 2 hour, after which 0.70 ml (11.2 mmol) methyl iodide was added dropwise, with external water bath cooling, and stirring continued for a further 16 h. The reaction mixture was then poured into 200 ml ice-cold water, and the precipitate collected by filtration, washed with hexane, and dried in vacuo to afford 1.12 g (71%) 2-(5-methoxymethyl-furan-2-carbonyl)-3,3-bis-methylsulfanyl-acrylonitrile as a brown crystalline solid. EI-MS m/e (%): 283 (M+, 7), 282 ([M—H]+, 6), 268 ([M—CH3]+, 50), 266 ([M—OH]+, 35), 252 ([M—OCH3]+, 21), 238 ([M—CH2OCH3]+, 100), 139 (61).

Provenance & Evidence