Chlorotrimethylsilane → HCID 68842549, compound

Participants

Reaction Steps

1M 2-phenylethylmagnesium chloride solution in THF (550 ml, 550 mmole) was added within 15 minutes under argon and while cooling with ice to a solution of 8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (39 g, 186 mmole) in THF (300 ml) and the mixture was then stirred for 16 hours at room temperature. The reaction mixture was worked up by adding saturated ammonium chloride solution (295 ml) and water (120 ml) while cooling with ice, and was extracted with diethyl ether (3×150 ml). The organic phase was washed with water (100 ml) and saturated NaCl solution (100 ml) and then concentrated by evaporation. A brown oil remained (60.4 g). The crude product was dissolved in ethyl methyl ketone (310 ml) and ClSiMe3 (35.6 ml, 282 mmole) was added while cooling with ice. After 16 hours at RT the resultant solid product was suction filtered and washed with ethyl methyl ketone.

Provenance & Evidence