Sulfuric Acid → HCID 10960808, compound

Participants

Reaction Conditions

Reaction Steps

To a 1 M solution of lithium aluminum hydride in ethyl ether (91.5 ml) was added dropwise at 0° C. a 7.2 M solution of sulfuric acid in THF (6.4 ml) and the mixture was stirred at 0° C. for 1 h. To the mixture at 0° C. was added 8 (10.9 g) in THF (75 ml). The reaction mixture was allowed to warm to RT and stirred for 3.5 h at RT at which point it was cooled back to 0° C. and a 30% (v/v) solution of H2O in THF was added dropwise. A 1 N solution of NaOH (15 ml) was added. The reaction mixture was filtered through a sintered glass funnel to remove the aluminum oxides. The filtrate was transferred to a separatory funnel and partitioned between water and ethyl ether. The aqueous layer was extracted three times with ether. The organic phase was dried (Na2SO4) and concentrated. The resulting oil was taken up in THF (175 ml). To the THF solution was added t-butanol (60 ml), N-methyl-morpholine-N-oxide (10.7 g) and osmium tetraoxide (2.5 wt % in t-butanol, 7.6 ml). The reaction mixture was stirred for 18 h at RT. The reaction mixture was transferred to a separatory funnel and partitioned between brine and ethyl acetate. The aqueous layer was extracted three times with ethyl acetate. The organic layer was dried, concentrated and the residue applied to a silica gel column. The product was eluted with 10% ethyl acetate/petroleum ether giving 9 (10.92 g).

Provenance & Evidence