Methanol → HCID 68773599, compound

Participants

Reaction Conditions

Reaction Steps

Na (22.7 mg, 0.987 mmol) was added to MeOH (24 ml). The resulting solution was treated at 25° C. with rel-(4R,5R)-1-(5-methylspiro[2.5]oct-6-en-4-yl)ethanone (1.62 g, 9.97 mmol, prepared in example 11), and heated at 80° C. for 64 h. The resulting solution was cooled, diluted pentane and poured into a saturated aqueous NH4Cl solution. The aqueous phase was extracted twice with pentane and the combined organic phases were washed with a saturated aqueous NaCl solution, dried (Na2SO4) and concentrated. FC (250 g SiO2, pentane/Et2O 10:0.5) of the crude product (1.5 g) gave rel-(4S,5R)-1-(5-methylspiro[2.5]oct-6-en-4-yl)ethanone (930 mg, 57%) and a rel-(4R,5R)-1-(5-methylspiro[2.5]oct-6-en-4-yl)ethanone/rel-(4S,5R)-1-(5-methylspiro[2.5]oct-6-en-4-yl)ethanone (60:40, 408 mg, 25%).

Provenance & Evidence