tert-Butanol → Ethyl 3-(6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)-3-cyclopropylpropanoate

Participants

Reaction Steps

Under an argon atmosphere, to a solution of 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (844 mg) in toluene (50 mL) were added copper (I) chloride (134 mg) and sodium tert-butoxide (130 mg), and the mixture was stirred at room temperature for 5 min. To the obtained yellow suspension were successively added ethyl 3-(6-(((tert-butyldiphenylsilyl)oxy)methyl)pyrimidin-4-yl)-3-cyclopropylacrylate (6.60 g), polymethylhydrosiloxane (8.10 mL) and tert-butyl alcohol (2.56 mL) at room temperature, and the mixture was directly stirred for 7 hr. To the reaction mixture was added methanol, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (6.70 g) as a pale-yellow oil.

Provenance & Evidence