Imidazole → tert-Butyl(chloro)phenylsilane

Participants

Reaction Steps

Synthesis was carried out with farnesol as a starting material. A protective group was bonded to the hydroxy group of farnesol using imidazole, anhydrous dimethylformamide, anhydrous dichloromethane, and tert-butyldiphenylsilyl chloride (TBDPS) to obtain a TBDPS-protected form (fi) (yield: 99%). Next, this compound was reacted with m-chloroperbenzoic acid in an anhydrous dichloromethane solvent to obtain an epoxy form (fii) (yield: 29%). The epoxy was subjected to periodic acid oxidation using orthoperiodic acid in a mixed solvent of ether and tetrahydrofuran to obtain an aldehyde form (fiii) (yield: 73%). A Grignard reagent was prepared from ethyl iodide and magnesium in an anhydrous ether solvent and then reacted with the aldehyde to form an alcohol form (fiv) (yield: 80%). The TBDPS group in the compound (fiv) was removed using tetrabutylammonium fluoride in an anhydrous tetrahydrofuran solvent to form a diol form (fv) (yield: 93%).

Provenance & Evidence