Ethylene Glycol → (1R,5S,6S,7R)-3,3-Ethylenedioxy-7-benzoyloxy-6-hydroxymethylbicyclo[3,3,0]octane

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Reaction Steps

320 mg. of the alcohol prepared according to Reference Example 1(o), 0.5 ml. of ethylene glycol, 4 mg. of p-toluenesulfonic acid, and 10 ml. of benzene are agitated for 1.5 hours with the use of a water trap at reflux temperature. The mixture is cooled, diluted with ether, shaken once with 4% sodium bicarbonate solution, washed neutral with water, dried over magnesium sulfate, and evaporated under vacuum, thus obtaining 390 mg. of the ketal as a colorless oil.

Provenance & Evidence