Boron trifluoride → HCID 9998962, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2.0 g 3-[3,5-dimethyl-4-(3-ethinylpropoxy)phenyl]-5-methyl-1,2,4-oxadiazole, prepared by a procedure similar to that described in Example 1(b), in 50 mls anhydrous tetrahydrofuran in an argon atmosphere was chilled to about -70° C. To this solution there was added 3.7 mls butyl lithium followed by ethyl trifluoroacetate and, after ten minutes, 1.5 mls boron trifluoride ethereate. The solution was stirred for five hours at -70° C. and then overnight without cooling, quenched with 20 mls aqueous ammonium chloride solution, diluted with water and extracted with ethyl ether. The ethyl ether extracts were dried (Na2SO4) and concentrated in vacuo. The residue was subjected to column chromatography (silica gel; 20:80 to 40:60 ethyl ether/hexane) to give 497 mg of the title compound as an oil.

Provenance & Evidence