2-[2-[tert-butyl(dimethyl)silyl]oxyethoxy]ethanol

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: 18.2 g of carbon tetrabromide is added over 15 minutes at −15°/−20° C. to a mixture containing 11.2 g of the product of Stage A and 14.4 g of triphenylphosphine in 100 cm3 of methylene chloride. Agitation is carried out for 1 hour 15 minutes at −15° C., the solvent is evaporated off, followed by taking up in pentane, agitating at ambient temperature, separating, washing with pentane and drying at 50° C. under reduced pressure. 10.1 g of expected product is obtained. the solvent is evaporated off separating washing with pentane drying at 50° C. under reduced pressure

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

Procedure: 18.2 g of carbon tetrabromide is added over 15 minutes at −15°/−20° C. to a mixture containing 11.2 g of the product of Stage A and 14.4 g of triphenylphosphine in 100 cm3 of methylene chloride. Agitation is carried out for 1 hour 15 minutes at −15° C., the solvent is evaporated off, followed by taking up in pentane, agitating at ambient temperature, separating, washing with pentane and drying at 50° C. under reduced pressure. 10.1 g of expected product is obtained. the solvent is evaporated off separating washing with pentane drying at 50° C. under reduced pressure

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

Procedure: 20 g of diethyleneglycol is added to 9.05 g of sodium hydride in 320 cm3 of tetrahydrofuran, the reaction medium is agitated for 45 minutes, 28.3 g of dimethylterbutylsilane chloride is added, agitation is carried out for 3 hours while leaving the temperature to return to ambient. Extraction is carried out with ether, followed by washing with an aqueous solution of sodium bicarbonate, with salt water, drying and evaporating the solvent. 40.25 g of expected product is obtained. agitation is carried out for 3 hours while leaving the temperature Extraction by washing with an aqueous solution of sodium bicarbonate, with salt water drying evaporating the solvent

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of oxalyl chloride (8.38 mL) in dichloromethane (470 mL) was cooled to −78° C. in a nitrogen atmosphere. A solution of dimethyl sulfoxide (8.01 mL) in dichloromethane (10 mL) was added dropwise to the reaction solution at the same temperature. The reaction solution was stirred at the same temperature for 10 minutes. A solution of 2-[2-(tert-butyldimethylsilanyloxy)ethoxy]ethanol (25.9 g) in dichloromethane (20 mL) was added dropwise to the reaction solution at the same temperature. The reaction solution was stirred at the same temperature for 30 minutes. Triethylamine (52.1 mL) was added to the reaction solution at the same temperature. The reaction solution was stirred for one hour while gradually returning to room temperature. Aqueous ammonium chloride was added to the reaction solution, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The organic layer was filtered through a silica pad and the filtrate was concentrated. Tetrahydrofuran (500 mL) was added to the residue. The reaction solution was cooled to −78° C. in a nitrogen atmosphere. Vinylmagnesium chloride (148 mL, 1.38 M solution in tetrahydrofuran) was added dropwise to the reaction solution at the same temperature. The reaction solution was heated to room temperature with stirring over six hours. Aqueous ammonium chloride and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (10.03 g). The reaction solution was stirred at the same temperature for 30 minutes The reaction solution was stirred for one hour while gradually returning to room temperature the organic layer was separated The organic layer was washed with saturated aqueous sodium chloride dried over anhydrous magnesium sulfate The organic layer was filtered through a silica pad the filtrate was concentrated Tetrahydrofuran (500 mL) was added to the residue Vinylmagnesium chloride (148 mL, 1.38 M solution in tetrahydrofuran) was added dropwise to the reaction solution at the same temperature The reaction solution was heated to room temperature with stirring over six hours Aqueous ammonium chloride and ethyl acetate were added to the reaction solution the organic layer was separated The organic layer was washed with saturated aqueous sodium chloride dried over anhydrous magnesium sulfate The organic layer was concentrated under reduced pressure The residue was purified by silica gel column chromatography

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of oxalyl chloride (8.38 mL) in dichloromethane (470 mL) was cooled to −78° C. in a nitrogen atmosphere. A solution of dimethyl sulfoxide (8.01 mL) in dichloromethane (10 mL) was added dropwise to the reaction solution at the same temperature. The reaction solution was stirred at the same temperature for 10 minutes. A solution of 2-[2-(tert-butyldimethylsilanyloxy)ethoxy]ethanol (25.9 g) in dichloromethane (20 mL) was added dropwise to the reaction solution at the same temperature. The reaction solution was stirred at the same temperature for 30 minutes. Triethylamine (52.1 mL) was added to the reaction solution at the same temperature. The reaction solution was stirred for one hour while gradually returning to room temperature. Aqueous ammonium chloride was added to the reaction solution, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The organic layer was filtered through a silica pad and the filtrate was concentrated. Tetrahydrofuran (500 mL) was added to the residue. The reaction solution was cooled to −78° C. in a nitrogen atmosphere. Vinylmagnesium chloride (148 mL, 1.38 M solution in tetrahydrofuran) was added dropwise to the reaction solution at the same temperature. The reaction solution was heated to room temperature with stirring over six hours. Aqueous ammonium chloride and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (10.03 g). The reaction solution was stirred at the same temperature for 30 minutes The reaction solution was stirred for one hour while gradually returning to room temperature the organic layer was separated The organic layer was washed with saturated aqueous sodium chloride dried over anhydrous magnesium sulfate The organic layer was filtered through a silica pad the filtrate was concentrated Tetrahydrofuran (500 mL) was added to the residue Vinylmagnesium chloride (148 mL, 1.38 M solution in tetrahydrofuran) was added dropwise to the reaction solution at the same temperature The reaction solution was heated to room temperature with stirring over six hours Aqueous ammonium chloride and ethyl acetate were added to the reaction solution the organic layer was separated The organic layer was washed with saturated aqueous sodium chloride dried over anhydrous magnesium sulfate The organic layer was concentrated under reduced pressure The residue was purified by silica gel column chromatography

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: To a solution of 5-(t-butyldimethylsilyloxy)-3-oxa-1-pentanol (2.16 g, 9.8 mmol) in dry tetrahydrofuran (20 ml) was added sodium hydride (432 mg, 60% in oil, 10.8 mmol) at room temperature. The mixture was stirred for 30 minutes, and propalgyl bromide (2.9 g, 19.6 mmol) was added thereto. The mixture was stirred at room temperature for 12 hours. After the reaction was completed, water was added thereto. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried over anhydrous sodium sulfate, and filtered. The organic solvent was removed under reduced pressure to give a crude product. This crude product thus obtained was subjected to silica gel column chromatography (n-hexane:ethyl acetate=8:1) to give the title compound (950 mg, yield: 38%). The mixture was stirred at room temperature for 12 hours The resulting mixture was extracted with ethyl acetate The organic layer was washed with saturated saline solution dried over anhydrous sodium sulfate filtered The organic solvent was removed under reduced pressure to give a crude product This crude product thus obtained

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

Procedure: 18.2 g of carbon tetrabromide is added over 15 minutes at −15°/−20° C. to a mixture containing 11.2 g of the product of Stage A and 14.4 g of triphenylphosphine in 100 cm3 of methylene chloride. Agitation is carried out for 1 hour 15 minutes at −15° C., the solvent is evaporated off, followed by taking up in pentane, agitating at ambient temperature, separating, washing with pentane and drying at 50° C. under reduced pressure. 10.1 g of expected product is obtained. the solvent is evaporated off separating washing with pentane drying at 50° C. under reduced pressure

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

Procedure: 20 g of diethyleneglycol is added to 9.05 g of sodium hydride in 320 cm3 of tetrahydrofuran, the reaction medium is agitated for 45 minutes, 28.3 g of dimethylterbutylsilane chloride is added, agitation is carried out for 3 hours while leaving the temperature to return to ambient. Extraction is carried out with ether, followed by washing with an aqueous solution of sodium bicarbonate, with salt water, drying and evaporating the solvent. 40.25 g of expected product is obtained. agitation is carried out for 3 hours while leaving the temperature Extraction by washing with an aqueous solution of sodium bicarbonate, with salt water drying evaporating the solvent