Synthesis of-3-(tert-butyldimethylsilyoxy)-4-Isopropylcyclopentanone (4)

Abstract

In this research the preparation of target compound was completed in three sequential steps. Starting from furfural alcohol (1) that was converted to racemic 4-hydroxycyclopent-2-enone (2) in 39% yield after treated with catalytic amount of KH2PO4 in water as a solvent. Protection of the free hydroxyl group in (2) with t-butyldimethylsilyl chloride in the presence of DMAP was the next step to furnish compound (3) in yield of 50%. Organocuprate conjugate addition on (3) provide compound (4) in yield of 50%.