Oxazole → 2-(Tris(propan-2-yl)silyl)-1,3-oxazole

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Reaction Conditions

Reaction Steps

Oxazole (10 g, 144.797 mmol) is dissolved in 400 mL abs. diethylether under argon. The solution is cooled to −78° C. and n-butyllithium (1.6 M solution in hexane, 100 mL, 160 mmol) is added slowly at that temperature. After stirring for 1 h triisopropylsilyl trifluoromethanesulfonate (40.265 mL, 144.797 mmol) in 100 mL abs. diethylether is added slowly. The mixture is warmed to r.t. within 12 h, and the solvent is evaporated in vacuo. The residue is treated with cyclohexane, filtered over silica gel, washed with cylcohexane/ethyl acetate 8:1, and the solvent is evaporated in vacuo. Yield: 33 g; ESI mass spectrum: [M+H]+=226; retention time HPLC: 1.428 min (HPLC method Z001_002).

Provenance & Evidence