(2S-trans)-2,3-bis[(benzyloxy)methyl]cyclobutanone → Dibenzyl ether

Participants

Reaction Conditions

Reaction Steps

A solution of (2S-trans) -2,3-bis [(benzyloxy) -methyl]cyclobutanone (0.2 g., 0.645 mmole) in toluene (4 ml.) was added dropwise over 10 minutes to a solution of triisobutylaluminum (0.91M in hexane, 0.9 ml., 0.816 mmole) in toluene (2 ml. ) at -40° C. The mixture was stirred at -50° C. for 4 hours and at -40° C for one hour. A solution of triisobutylaluminum (1 ml., 0.91 mmole) was added to the reaction mixture. After stirring for 30 minutes the reaction was quenched by adding 10% hydrochloric acid (2 ml.) at -40° C. The organic phase was washed with brine, dried (magnesium sulfate), and the solvent was evaporated to give [1S-(1α, 2β, 3β)]-3-hydroxy-2-cyclobutane-dimethanol, dibenzyl ether; TLC (30% ethyl acetate/hexane) Rf =0.3. The product contained about 5% of the isomeric compound; TLC (30% ethyl acetate/hexane) Rf =0.2.

Provenance & Evidence