Pivalic acid → HCID 131719272, compound

Participants

Reaction Steps

7-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-1-tert-butyldimethyl-silyloxy-6-hydroxy-5-methylhept-4-ene (4.74 g) was dissolved in triethyl orthoacetate (76 ml) and pivalic acid (171mg) was added. The solution was placed in an oil bath preheated to 130° C., and stirred for 21/2 hrs. ter cooling, the reaction was diluted with ether, washed with 1N NaHSO4 (3X), saturated sodium bicarbonate, brine, and dried. The solvent was evaporated and the resulting oil chromatographed on silica gel (20% ethyl acetate in hexanes) to give ethyl (E) 6-(4-tert-butyldimethylsilyloxy-1,3-dihydro-6-methoxy-7-methyl-3-oxoisobenzofuran-5-yl)-3-(3-tert-butyldimethylsilyloxypropyl)-4-methylhex-4-enoate (2.94 g), a compound of Formula 802.

Provenance & Evidence