Carbon tetrabromide → HCID 18988272, compound

Participants

Reaction Conditions

Reaction Steps

Part B. The alcohol from Part A above is dissolved in methylene chloride along with carbon tetrabromide, and cooled to 0° C. A methylene chloride solution of triphenylphosphine is added dropwise. The mixture is stirred for 14 hours, then evaporated and rapidly eluted through a plug ofsilica gel with an appropriate solvent system to afford 2-bromomethyl-3,6-dihydro-4,5-dipentyl-2H-thiopyran. This compound is useddirectly, and treated with potassium cyanide in dimethylsulfoxide at 80° C. until thin-layer chromatography shows the reaction is complete. At this point, the solution is cooled, and poured into 4 volumesof water. This mixture is extracted with ethyl acetate, and the extract is washed with more water (3× an equal volume), then brine, then dried over anhydrous magnesium sulfate, filtered and evaporated. Chromatography will then purify the product, (3,6-dihydro-4,5-dipentyl-2H-thiopyran-2-yl)acetonitrile.

Provenance & Evidence