Chlorotrimethylsilane → 4-Methoxy-2,2,8,8-tetramethyl-6-methylidene-3,7-dioxa-2,8-disilanon-4-ene

Participants

Reaction Conditions

Reaction Steps

To dry diisopropylamine (52 mL, 0.39 mol) in THF (400 mL) at 0° C. under nitrogen was added n-BuLi (146 mL, 2.5M in hexanes, 0.365 mol) followed by TMEDA (48.5 mL, 0.32 mol). The solution was stirred at 0° C. for 30 min then cooled to -78° C. Methyl 3-trimethylsiloxybut-2-enoate, 1, (57.6 g, 0.3 mol) was added to the solution. After stirring for 10 min, chlorotrimethylsilane (61 mL, 0.48 mol) was added. The mixture was allowed to warm up to 0° C. and was then concentrated to dryness on a rotary evaporator at 0° C. (the compound is heat sensitive). Hexanes (dried over molecular sieves; 1 L) were added. The insolubles were removed by filtration and washed with hexanes. The combined filtrate was concentrated to dryness on a rotary evaporator at 0° C. and dried overnight, under high vacuum, at room temperature, to afford 82 g of crude product, 2, which was used in the next step without further purification.

Provenance & Evidence