chloromethyl-dimethyl-phenylsilane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Mix 2,6-di-t-butyl-4-mercaptophenol (2.4 g, 10 mmol), potassium carbonate (1.4 g, 10 mmol), chloromethyldimethylphenylsilane (1.9 g, 10 mmol) and dimethylformamide (50 mL) and stir overnight at room temperature under argon atmosphere. Dilute the mixture with ice-water and extract with ethyl ether. Wash the ethereal layer with water, then brine, filter through flourosil-Na2SO4, and evaporate to an orange oil (3.5 g). Purify the product by first distilling (bp 160-170° C. @ 0.1 mm Hg), then subjecting to silica gel chromatography (CCl4 :CHCl3 /1:1) to obtain the title compound as a light yellow oil which slowly crystallizes to a white waxy solid (2.3 g, 59%). Anal. Calcd for C23H34OSSi: C, 71.44; H, 8.86; S, 8.29; Found: C, 71.14; H, 8.86; S, 7.98. extract with ethyl ether Wash the ethereal layer with water brine, filter through flourosil-Na2SO4 evaporate to an orange oil (3.5 g) Purify the product by first distilling (bp 160-170° C. @ 0.1 mm Hg)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Mix 2,6-di-t-butyl-4-mercaptophenol (2.4 g, 10mmol), potassium carbonate (1.4 g, 10 mmol), chloromethyldimethylphenylsilane (1.9 g, 10 mmol) and dimethylformamide (50 mL) and stir overnight at room temperature under argon atmosphere. Dilute the mixture with ice-water and extract with ethyl ether. Wash the ethereal layer with water, then brine, filter through flourosil-Na2SO4, and evaporate to an orange oil (3.5 g). Purify the product by first distilling (bp 160°-170° C. @0.1 mm Hg), then subjecting to silica gel chromatography (CCl4 :CHCl3 /1:1) to obtain the title compound as a light yellow oil which slowly crystallizes to a whim waxy solid (2.3 g, 59%). extract with ethyl ether Wash the ethereal layer with water brine, filter through flourosil-Na2SO4 evaporate to an orange oil (3.5 g) Purify the product by first distilling (bp 160°-170° C. @0.1 mm Hg)

Conditions: temp:-10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 7.9 g (0.329 mole) of magnesium metal and 0.5 mL of 1,2-dibromoethane in 150 mL of diethyl ether was added dropwise a solution of 50 g (0.271 mole) of (chloromethyl)dimethylphenylsilane in 100 mL of diethyl ether. The addition required 30 minutes. Upon completion of addition, the resultant solution was transferred using a cannula to a flask containing 15.5 g (0.108 mole) of copper(I) bromide which was under a nitrogen atmosphere and was cooled in a dry ice/acetone bath. To this flask was added dropwise a solution 10.8 g (0.108 mole) of ethyl acrylate in 50 mL of diethyl ether. The addition required 40 minutes. Upon completion of addition, the reaction mixture was allowed to warm to -10° C. It was then diluted with 400 mL of diethyl ether, and a solution of 14.2 g of ammonium chloride in 40 mL of water was added dropwise while maintaining the temperature at -10° C. to 0° C. Upon completion of addition, the reaction mixture was filtered, and the solvent was evaporated under reduced pressure, leaving a residue. This residue was passed through a column of silica gel, eluting with diethyl ether/petroleum ether (5:95). The product-containing fractions were combined, and the solvent was evaporated, yielding 12.95 g of ethyl 5-methyl-5-phenyl-5-silahexanoate as an oil. The addition required 30 minutes Upon completion of addition was cooled in a dry ice/acetone bath The addition required 40 minutes Upon completion of addition while maintaining the temperature at -10° C. to 0° C Upon completion of addition the reaction mixture was filtered the solvent was evaporated under reduced pressure leaving a residue eluting with diethyl ether/petroleum ether (5:95) the solvent was evaporated