HCID 86747698, compound → HCID 19091489, compound

Participants

Reaction Steps

To a stirred solution of 0.444 g of the product of Example 4 in 10 ml of tetrahydrofuran, cooled to 0° C. is slowly added 0.656 ml of 3.0 M methylmagnesium bromide. The cooling bath is removed after 0.5 hour and reaction mixture allowed to warm to room temperature and stir for 2 hours. An additional 1.2 ml of 3.0 M methyl magnesium bromide is added and the reaction mixture stirred at room temperature for 0.5 hour. An additional 1.0 ml of 3.0 M methyl magnesium bromide is added an the reaction mixture stirred at room temperature for 0.5 hour. The reaction mixture is quenched with saturated ammonium chloride and diluted with water, followed by extraction with ethyl acetate. The organic layer is dried with MgSO4, filtered and concentrated to give a crude solid which is purified by column chromatography on silica gel with 1:2 ethyl acetate-hexane to give 0.706 g of the desired product as a solid. FAB MASS SPEC 693(M+ H).

Provenance & Evidence