1,4-Cyclohexadiene → 1-(5-Hydroxymethyl-1,3,4-oxadiazol-2-yl)-7-phenoxy-heptan-1-one

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Reaction Steps

To a stirred suspension of 73.1 (80 mg, 0.2 mmol) and Pd/C (160 mg) in AcOH/MeOH (1:10 mixture, 5 mL) at 45° C. was added 1,4-cyclohexadiene (304 mg, 4 mmol) over a period of 30 min. The mixture was stirred for an additional 2 h at the same temperature. The catalyst was removed by filtration through celite and the filtrate was evaporated under reduced pressure. The residue was purified through a column of silica, eluting with 45% ethyl acetate in petroleum ether to give 74.1 as a white solid (m p 83-85° C.) in 25% yield (15 mg).

Provenance & Evidence