Pivalic acid → HCID 131719271, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-[2-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)-1-hydroxyeth-1-yl]cyclopent-1-ene (0.22 g) in triethylorthoacetate (10 ml) was treated with pivalic acid (0.010 g) and then heated to 100° C., and maintained at that temperature for 18 hours. After cooling to ambient temperature, the solution was diluted with 1:1 ethyl acetate:hexanes and washed sequentially with water, saturated aqueous sodium bicarbonate, and brine. Drying over magnesium sulfate was followed by evaporation; chromatography of the residue on silica gel (10% ethyl acetate in hexanes) afforded ethyl (E) 2-[2-[2-[4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl]ethylidene]-cyclopent-1-yl]acetate (0.11 g) as an oil.

Provenance & Evidence