Chlorotrimethylsilane → HCID 86626439, compound

Participants

Reaction Steps

n-Butyllithium (1.6 M in n-hexane, 2.8 mL, 2.76×1.6 mmol) was added dropwise to a dry THF (6.6 mL) solution of 2-methoxy-6-(trimethylsilyl)pyridine (MTP, 0.500 g, 2.76 mmol) under an argon atmosphere at between −15° C. and 0° C. (this temperature was kept during the reaction) and stirred for 1 hour, and a dry THF (2 mL) solution of FEO (0.434 g, 2.76×1.2 mmol) was then added dropwise and stirred for 1 hour. Subsequently, n-butyllithium (1.6 M in n-hexane, 2.4 mL, 2.76×1.4 mmol) was added dropwise and stirred for 1 hour, and a dry THF (3 mL) solution of chlorotrimethylsilane (697 μL, 2.76×2.0 mmol) was then added dropwise and stirred for 1 hour. The temperature was raised to room temperature, followed by adding water, brine, and n-hexane (50 mL). The organic layer was separated, dried over Na2SO4, filtered, and then concentrated to dryness. The residue was purified by medium pressure silica gel column chromatography (n-hexane), and desired fractions were combined and concentrated to dryness. TMS-MTPC (0.305 g, 1.08 mmol, 39%) was obtained as a colorless transparent liquid.

Provenance & Evidence