Synthesis of substituted 5-diethoxymethyl-5-ethyloxazolidines

✍ Scribed by S. Nakhar; I. G. Tishchenko; O. N. Bubel'; V. I. Biba

• Book ID: 104782023
• Publisher: Springer US
• Year: 1987
• Tongue: English
• Weight: 345 KB
• Volume: 23
• Category: Article
• ISSN: 0009-3122
• DOI: 10.1007/bf00475658

✦ Synopsis

The preparative experiments were carried out by the method described below. A l-mmole portion of 2,4,6-triarylverdazyl [i] and i mmole of dicyanobromomethane [8] or cyanoethoxycarbonylbromomethane are mixed together in 25 ml of benzene. On the following day the precipitated mixture of salts is filtered, dried, and analyzed for the content of salt II (Amax, r [i]), and also for the total bromide ion content. From this, the amount of the hydrobromide salt of III is found. The filtrate is evaporated to a min~l volume and the mixture of compounds (see Table i, experiments 4, 5) is separated in a thin layer of Silpearl brand silica gel, with elution by benzene (development in UV light). The reaction product is washed with acetonitrile. After the evaporation of solvent, the residue is crystallized from ethanol.

In experiments i, 2, 3, 6, and 7 (Table i), the filtrate is evaporated to dryness in an aspirator, and the fragmentation product is extracted from the residue by multiple extraction by a 3:1 hexane--benzene mixture.

Since verdazyl If is slightly soluble in benzene, the preparative experiments were carried out in its mixture with acetonitrile (1:2).