Pivalic acid → HCID 131719272, compound

Participants

Reaction Steps

(E)-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 (171 mg) was added. The solution was placed in an oil bath preheated to 130° C., and stirred for 2 1/2 hrs. After cooling, the reaction was diluted with ether, washed with 1N NaHSO4 (3×), 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