chloromethyl(trimethyl)silane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A solution of 15 g. (0.057 mole) of 2-methyl-3-(4-methoxybenzoyl)indole in 120 ml. of DMF under nitrogen was treated with 1.36 g. (0.057 mole) of sodium hydride at 0° C. The mixture was allowed to warm to room temperature over a period of two hours and then treated with 20 ml. of chloromethyl trimethylsilane and a catalytic amount of sodium iodide and stirred at room temperature for about twelve hours. The solvent was removed by distillation in vacuo, the residue was mixed with 500 ml. of diethyl ether and the mixture filtered. The filtrate was taken to dryness, and the residue was chromatographed on silica gel, eluting with 30% ethyl acetate/hexane. The product, consisting of 16.5 g. of 2-methyl-3-(4-methoxybenzoyl)-1-trimethylsilylmethyl-1H-indole, was isolated as a light amber oil from the initial, more mobile fractions. at 0° C treated with 20 ml The solvent was removed by distillation in vacuo the residue was mixed with 500 ml of diethyl ether and the mixture filtered the residue was chromatographed on silica gel eluting with 30% ethyl acetate/hexane

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 300 mmol of Methylacrylic acid (MAA) and 200 mmol of chloromethyl trimethylsilane were dissolved in 400 ml of dimethylamide. Potassium carbonate was added to the solution and heated to 90° C. and stirred for 5 hours. Next, the reaction solution was filtered. The filtrate was added to a sodium hydrogen carbonate solution, extracted with ether and pure water respectively, dried, filtered, and concentrated to obtain trimethylsilanylmethyl methylacrylate (TMSA) having the formula (i) below Next, the reaction solution was filtered The filtrate was added to a sodium hydrogen carbonate solution extracted with ether and pure water respectively dried filtered concentrated

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 118 mL (1.57 mol) of allylamine warmed at 40° C. in an inert atmosphere was very slowly added 100 mL (0.72 mol) of chloromethyl trimethylsilane (approximate rate of 1 mL/min). The reaction mixture was slowly warmed to 70° C. and stirred for 24 h. The reaction mixture was cooled to 0° C. and to it was added water to break tip the gel and then 300 mL of 2N NaOH solution. The reaction mixture was extracted with ether. The combined organic fractions were washed with 500 mL of sat'd NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by distillation (bp 80-84° C. @ 100 torr) to give 75 g of the title compound. The reaction mixture was cooled to 0° C. and to it The reaction mixture was extracted with ether The combined organic fractions were washed with 500 mL of sat'd NaCl solution dried over Na2SO4 filtered the filtrate was concentrated The residue was purified by distillation (bp 80-84° C. @ 100 torr)