Rapid reduction of alkyl tosylates with lithium triethylborohydride. A convenient and advantageous procedure for the deoxygenation of simple and hindered alcohols. Comparison of various hydride reagents

Lithium triethylborohydride (super-hydride) in tetrahydrofuran reduces the p-toluenesulfonates of primary and secondary alcohols to the corresponding alkanes in excellent yields. The reaction is general and applicable even to tosylates derived from cycloalkanols, hindered alcohols, and polyhydroxy derivatives. Examination of the scope of the reaction and comparison with the results realized with other hydridic reducing agents reveals the advantages of this new procedure.