Methanol → 7-Hydroxy-3-methoxybicyclo[4,3,0]non-3-ene

Participants

Reaction Conditions

Reaction Steps

Diisobutylaluminium hydride (28.5 ml) was added dropwise to a stirred solution of 3-methoxybicyclo[4,3,0]non-3-en-7-one (20 g; prepared as described in Reference Example 1) in diethyl ether (600 ml), with cooling to -10° C. The resulting solution was stirred at 0° C. for 3 hours and then it was treated with methanol (20 ml). A gelatinous precipitate was formed, and the mixture was then treated with anhydrous sodium sulphate (200 g) and filtered with the aid of diatomaceous earth. The filtrate was concentrated at reduced pressure, to give 7-hydroxy-3-methoxybicyclo[4,3,0]non-3-ene (16 g).

Provenance & Evidence