4-Methoxybenzyl alcohol → HCID 86604216, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4.1 g (29.6 mmol) of 4-methoxybenzyl alcohol in 100 mL of THF was added 7.76 g (29.6 mmol) of triphenylphosphine and 8.53 g (22.8 mmol) of 2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-1,1,1,3,3,3-hexafluoro-propan-2-ol at room temperature. The reaction mixture was cooled to 0° C. and 5.7 mL (29.6 mmol) of diisopropylazo dicarboxylate were added. The solution was stirred at room temperature overnight, a solution of NH4Cl was added and the inorganic layer was extracted with ethyl acetate. The combined layers were washed with brine, and dried (Na2SO4), filtered and evaporated. Column chromatography with ethyl acetate/n-heptane 1:99 as eluent yielded 8.39 g (74%) of tert-butyl-dimethyl-{4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-silane as a light yellow liquid, MS: 494 (M)+.

Provenance & Evidence