butoxy(trimethyl)silane

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

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

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6 g of oxo-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetic acid ethyl ester and 2.6 g of butoxytrimethylsilane were dissolved in 200 ml of methylene chloride. The solution was cooled to 0° C., treated with 400 mg of trimethylsilyl triflate and stirred at 0° C. for 1.5 hours. After the dropwise addition of 2 g of triethylsilane, the reaction mixture was stirred at room temperature for 26 hours, then diluted with 500 ml of water, acidified with 2N hydrochloric acid and extracted with ether. The organic phase was washed with water, dried (Na2SO4) and the solvent evaporated. The oily residue was purified with flash chromatography (silica gel, eluent hexane/tert.butyl methyl ether 3%) and preparative HPLC (YMC CN 60 Å5-15 μm, hexane) to give 3.5 g of the title product as colorless oil. the reaction mixture was stirred at room temperature for 26 hours extracted with ether The organic phase was washed with water dried (Na2SO4) the solvent evaporated The oily residue was purified with flash chromatography (silica gel, eluent hexane/tert.butyl methyl ether 3%) and preparative HPLC (YMC CN 60 Å5-15 μm, hexane)

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

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4.40 g (40.5 mmol) of chlorotrimethylsilane were added dropwise while stirring at 0° C. to a solution of 3.00 g (40.5 mmol) of 1-butanol and 11.1 g (135 mmol) of 1-methylimidazole. The reaction mixture was stirred at from 0 to 5° C. for a further 15 min and at 20° C. for 15 min to form a liquid biphasic mixture. Removal of the upper phase gave 5.30 g (theory: 5.93 g) of 1-trimethylsilyloxybutane as a colorless oil having a purity of 90% (GC). to form a liquid biphasic mixture Removal of the upper phase

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

Procedure: 1 mole of n-butanol and 1.5 moles of trimethylchlorosilane were heated to reflux (54°-91° C.) with the addition of 0.0005 moles of tetra-n-butyl ammonium bromide. Vigorous evolution of HCl was observed. When evolution of gas ceased, the IR spectrum did not show an OH band. When the product was worked up by distillation, pure 1-trimethylsiloxybutane was obtained as distillate. to reflux (54°-91° C.) When the product was worked up by distillation

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

Procedure: 1 mole of n-butanol and 1.5 moles of trimethylchlorosilane were heated to reflux (54°-91° C.) with the addition of 0.0005 moles of tetra-n-butyl ammonium bromide. Vigorous evolution of HCl was observed. When evolution of gas ceased, the IR spectrum did not show an OH band. When the product was worked up by distillation, pure 1-trimethylsiloxybutane was obtained as distillate. to reflux (54°-91° C.) When the product was worked up by distillation

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4.40 g (40.5 mmol) of chlorotrimethylsilane were added dropwise to a solution of 3.00 g (40.5 mmol) of 1-butanol and 11.1 g (135 mmol) of 1-methylimidazole while stirring at 0° C. The reaction mixture was stirred for another 15 minutes at 0-5° C. and for 15 minutes at 20° C., resulting in the formation of a liquid two-phase mixture. The upper phase was separated off to give 5.30 g (theory: 5.93 g) of 1-trimethylsilyloxybutane as a colorless oil having a purity of 90% (GC). The reaction mixture was stirred for another 15 minutes at 0-5° C. and for 15 minutes at 20° C. resulting in the formation of a liquid two-phase mixture The upper phase was separated off

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6 g of oxo-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetic acid ethyl ester and 2.6 g of butoxytrimethylsilane were dissolved in 200 ml of methylene chloride. The solution was cooled to 0° C., treated with 400 mg of trimethylsilyl triflate and stirred at 0° C. for 1.5 hours. After the dropwise addition of 2 g of triethylsilane, the reaction mixture was stirred at room temperature for 26 hours, then diluted with 500 ml of water, acidified with 2N hydrochloric acid and extracted with ether. The organic phase was washed with water, dried (Na2SO4) and the solvent evaporated. The oily residue was purified with flash chromatography (silica gel, eluent hexane/tert.butyl methyl ether 3%) and preparative HPLC (YMC CN 60 Å5-15 μm, hexane) to give 3.5 g of the title product as colorless oil. the reaction mixture was stirred at room temperature for 26 hours extracted with ether The organic phase was washed with water dried (Na2SO4) the solvent evaporated The oily residue was purified with flash chromatography (silica gel, eluent hexane/tert.butyl methyl ether 3%) and preparative HPLC (YMC CN 60 Å5-15 μm, hexane)

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

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4.40 g (40.5 mmol) of chlorotrimethylsilane were added dropwise while stirring at 0° C. to a solution of 3.00 g (40.5 mmol) of 1-butanol and 11.1 g (135 mmol) of 1-methylimidazole. The reaction mixture was stirred at from 0 to 5° C. for a further 15 min and at 20° C. for 15 min to form a liquid biphasic mixture. Removal of the upper phase gave 5.30 g (theory: 5.93 g) of 1-trimethylsilyloxybutane as a colorless oil having a purity of 90% (GC). to form a liquid biphasic mixture Removal of the upper phase

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

Procedure: 1 mole of n-butanol and 1.5 moles of trimethylchlorosilane were heated to reflux (54°-91° C.) with the addition of 0.0005 moles of tetra-n-butyl ammonium bromide. Vigorous evolution of HCl was observed. When evolution of gas ceased, the IR spectrum did not show an OH band. When the product was worked up by distillation, pure 1-trimethylsiloxybutane was obtained as distillate. to reflux (54°-91° C.) When the product was worked up by distillation