3,3,3-Trifluoropropyl-trimethoxysilane → 3,3,3-Trifluoropropyl(tert-butyl)dimethoxy silane

Participants

Reaction Conditions

Reaction Steps

Under nitrogen, a 500 ml Schlenk flask was cooled to 0° C. and charged with 150 ml hexane and 3,3,3-trifluoropropyl trimethoxy silane (0.075 mol, 15 ml). A nitrogen purged addition funnel was fitted to the flask and charged with tert-butyllithium (0.075 mol, 34 ml). This was added dropwise to the cooled flask creating a cloudy, white precipitate (LiOCH3). After addition (1 hour), the addition funnel was washed with 20 ml of hexane. The ice bath was removed and the reaction mixture was allowed to warm to room temperature. The flask was fitted with a reflux condenser and the reaction mixture refluxed for two hours. After cooling to room temperature, the reaction mixture was filtered through a medium porosity filter tube, using Celite diatomaceous earth and glass wool as a filtering aid. A white solid was collected, which weighed 11.13 g wet (theoretical=3.0 grams of LiOCH3). The hexane was removed from the filtrate to give 20.33 g of a clear yellow oil.

Provenance & Evidence