Sulfuric Acid → (1S,5R,6S,7R)-6-Formyl-7-methyl-2-oxabicyclo[3,3,0]octan-3-one

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Reaction Steps

At 5°, a solution of 15 g. of the compound prepared according to Example 1(c) in 500 ml. of absolute methylene chloride is added to a solution of 136 g. of freshly prepared Collins reagent in 1 l. of absolute methylene chloride. The mixture is agitated for 30 minutes, combined with 2.5 l. of ether, and shaken in succession four times with respectively 150 ml. of 4% sodium bicarbonate solution, twice with respectively 175 ml. of 10% sulfuric acid, and four times with respectively 150 ml. of brine. After drying over magnesium sulfate, the mixture is evaporated under vacuum, thus obtaining 11.2 g. of the title compound as a brown oil.

Provenance & Evidence