Imidazole → [(6-Chlorohexyl)oxy](1,1-dimethylethyl)dimethylsilane

A 250 ml, three-necked flask was fitted with a large magnetic, egg-shaped stir bar, a thermocouple, reflux condenser, and an argon inlet. This apparatus was dried in an oven overnight at 125° C., assembled hot, and allowed to cool to room temperature in a stream of argon. The flask was charged with 15.09 grams (0.100 mole, 1.00 equivalents) of t-butyldimethylsilyl chloride, and 100 grams of cyclohexane. The silyl chloride rapidly dissolved, endothermically. 6-Chloro-1-hexanol, 13.96 grams (0.100 mole, 1.00 equivalent) was then weighed into the flask. After stirring at room temperature for fifteen minutes, the reaction mixture appeared hazy. The stirrer was halted, and a second, immiscible layer was observed in the bottom of the flask. Imidazole, 6.81 grams (0.100 mole, 1.00 equivalent) was then added to the reaction mixture. A fine white precipitate rapidly developed. The reaction mixture was stirred at room temperature, and monitored by GC analysis. An aliquot of the clear supernatant was injected into the GC. After five hours, both starting materials were still present, and the conversion to the desired product was 82.2%. The reaction mixture was stirred overnight at room temperature, under a blanket of argon. The sample after 30 hours indicated all the starting material had been consumed, with the formation of a single, higher boiling component. The reaction mixture was transferred to a small, dry, Chemglass pressure filter. The filtrate was collected in a dry, 500 ml flask. The filter cake was rinsed with additional cyclohexane (2×100 ml). The solvent was removed on the rotary evaporator, with the bath temperature set at 40° C.

1. customA 250 ml, three-necked flask was fitted with a large magnetic, egg-shaped stir bar
2. temperaturea thermocouple, reflux condenser, and an argon inlet
3. customThis apparatus was dried in an oven overnight at 125° C.
4. stirringThe reaction mixture was stirred at room temperature

ORD 기록

ord-8031cb18f98e448cbc369234e24f9bdd

출처 데이터셋

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US05493044