chloro-ethyl-dimethylsilane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 100 mL flame-dried three-necked flask, fitted with refluxing condenser and dropping funnel, magnesium (92 mg, 3.82 mmol), iodine (1 mg) and dry THF (6 mL) were placed under nitrogen. A light brown solution formed, the mixture was heated to reflux, and a solution of 3-bromophenoxydimethylsilane (0.899 g, 3.47 mmol) in THF (20 mL) was added by dropping funnel over 2 hr. The reaction mixture was refluxed overnight and cooled to room temperature. Ethyldimethylchlorosilane (0.681 g, 0.78 mL, 5.55 mmol) was then added by syringe. The reaction mixture was brought to reflux again for 6 hr, and allowed to stir overnight at room temperature. The reaction was then quenched with 1N HCl, and the reaction concentrated in vacuo. Extraction with CH2Cl2, aqueous workup, and column chromatography (n-hexane/ethyl acetate 8:1) yielded 3-ethyldimethylsilyl phenol (0.130 g, 0.73 mmol, 21%) as a colorless oil. In a 100 mL flame-dried three-necked flask, fitted with refluxing condenser A light brown solution formed the mixture was heated to reflux over 2 hr The reaction mixture was refluxed overnight to reflux again for 6 hr The reaction was then quenched with 1N HCl the reaction concentrated in vacuo Extraction with CH2Cl2, aqueous workup, and column chromatography (n-hexane/ethyl acetate 8:1)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 100 mL flame-dried three-necked flask, fitted with refluxing condenser and dropping funnel, magnesium (92 mg, 3.82 mmol), iodine (1 mg) and dry THF (6 mL) were placed under nitrogen. A light brown solution formed, the mixture was heated to reflux, and a solution of 3-bromophenoxydimethylsilane (0.899 g, 3.47 mmol) in THF (20 mL) was added by dropping funnel over 2 hr. The reaction mixture was refluxed overnight and cooled to room temperature. Ethyldimethylchlorosilane (0.681 g, 0.78 mL, 5.55 mmol) was then added by syringe. The reaction mixture was brought to reflux again for 6 hr, and allowed to stir overnight at room temperature. The reaction was then quenched with 1N HCl, and the reaction concentrated in vacuo. Extraction with CH2Cl2, aqueous workup, and column chromatography (n-hexane/ethyl acetate 8:1) yielded 3-ethyldimethylsilyl phenol (0.130 g, 0.73 mmol, 21%) as a colorless oil. In a 100 mL flame-dried three-necked flask, fitted with refluxing condenser A light brown solution formed the mixture was heated to reflux over 2 hr The reaction mixture was refluxed overnight to reflux again for 6 hr The reaction was then quenched with 1N HCl the reaction concentrated in vacuo Extraction with CH2Cl2, aqueous workup, and column chromatography (n-hexane/ethyl acetate 8:1)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 3-bromophenol (0.60 g, 3.47 mmol) in dry THF (15 mL) under nitrogen was added Et3N (0.48 mL, 3.47 mmol). A clear yellow solution formed immediately; after cooling to 0° C., dimethylethylsilyl chloride (0.43 g, 0.49 mL, 3.47 mmol) was added by syringe over a period of 10 minutes. The yellow color disappeared in 10 min, and a white cloudy solution formed. After 3 hr the thick reaction mixture was filtered, washed with 15 mL of hexane, and filtered again. Concentration gave a clear oil (quantitative weight recovery) that was used in the next step without any purification. A clear yellow solution formed immediately a white cloudy solution formed After 3 hr the thick reaction mixture was filtered washed with 15 mL of hexane filtered again Concentration gave a clear oil (quantitative weight recovery) that was used in the next step without any purification

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: According to the procedure as described in Example 1,2,2-dimethyl-1-methoxy-3-[(ethyldimethylsilyl)oxy]propane was prepared from intermediate 2,2-dimethyl-3-methoxy-1-propanol and reagent ethyldimethylsilyl chloride.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: According to the procedure as described in Example 1,2,2-dimethyl-1-methoxy-3-[(ethyldimethylsilyl)oxy]propane was prepared from intermediate 2,2-dimethyl-3-methoxy-1-propanol and reagent ethyldimethylsilyl chloride.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 100 mL flame-dried three-necked flask, fitted with refluxing condenser and dropping funnel, magnesium (92 mg, 3.82 mmol), iodine (1 mg) and dry THF (6 mL) were placed under nitrogen. A light brown solution formed, the mixture was heated to reflux, and a solution of 3-bromophenoxydimethylsilane (0.899 g, 3.47 mmol) in THF (20 mL) was added by dropping funnel over 2 hr. The reaction mixture was refluxed overnight and cooled to room temperature. Ethyldimethylchlorosilane (0.681 g, 0.78 mL, 5.55 mmol) was then added by syringe. The reaction mixture was brought to reflux again for 6 hr, and allowed to stir overnight at room temperature. The reaction was then quenched with 1N HCl, and the reaction concentrated in vacuo. Extraction with CH2Cl2, aqueous workup, and column chromatography (n-hexane/ethyl acetate 8:1) yielded 3-ethyldimethylsilyl phenol (0.130 g, 0.73 mmol, 21%) as a colorless oil. In a 100 mL flame-dried three-necked flask, fitted with refluxing condenser A light brown solution formed the mixture was heated to reflux over 2 hr The reaction mixture was refluxed overnight to reflux again for 6 hr The reaction was then quenched with 1N HCl the reaction concentrated in vacuo Extraction with CH2Cl2, aqueous workup, and column chromatography (n-hexane/ethyl acetate 8:1)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 3-bromophenol (0.60 g, 3.47 mmol) in dry THF (15 mL) under nitrogen was added Et3N (0.48 mL, 3.47 mmol). A clear yellow solution formed immediately; after cooling to 0° C., dimethylethylsilyl chloride (0.43 g, 0.49 mL, 3.47 mmol) was added by syringe over a period of 10 minutes. The yellow color disappeared in 10 min, and a white cloudy solution formed. After 3 hr the thick reaction mixture was filtered, washed with 15 mL of hexane, and filtered again. Concentration gave a clear oil (quantitative weight recovery) that was used in the next step without any purification. A clear yellow solution formed immediately a white cloudy solution formed After 3 hr the thick reaction mixture was filtered washed with 15 mL of hexane filtered again Concentration gave a clear oil (quantitative weight recovery) that was used in the next step without any purification

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a 100 mL flame-dried three-necked flask, fitted with refluxing condenser and dropping funnel, magnesium (92 mg, 3.82 mmol), iodine (1 mg) and dry THF (6 mL) were placed under nitrogen. A light brown solution formed, the mixture was heated to reflux, and a solution of 3-bromophenoxydimethylsilane (0.899 g, 3.47 mmol) in THF (20 mL) was added by dropping funnel over 2 hr. The reaction mixture was refluxed overnight and cooled to room temperature. Ethyldimethylchlorosilane (0.681 g, 0.78 mL, 5.55 mmol) was then added by syringe. The reaction mixture was brought to reflux again for 6 hr, and allowed to stir overnight at room temperature. The reaction was then quenched with 1N HCl, and the reaction concentrated in vacuo. Extraction with CH2Cl2, aqueous workup, and column chromatography (n-hexane/ethyl acetate 8:1) yielded 3-ethyldimethylsilyl phenol (0.130 g, 0.73 mmol, 21%) as a colorless oil. In a 100 mL flame-dried three-necked flask, fitted with refluxing condenser A light brown solution formed the mixture was heated to reflux over 2 hr The reaction mixture was refluxed overnight to reflux again for 6 hr The reaction was then quenched with 1N HCl the reaction concentrated in vacuo Extraction with CH2Cl2, aqueous workup, and column chromatography (n-hexane/ethyl acetate 8:1)

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of 3-bromophenol (0.60 g, 3.47 mmol) in dry THF (15 mL) under nitrogen was added Et3N (0.48 mL, 3.47 mmol). A clear yellow solution formed immediately; after cooling to 0° C., dimethylethylsilyl chloride (0.43 g, 0.49 mL, 3.47 mmol) was added by syringe over a period of 10 minutes. The yellow color disappeared in 10 min, and a white cloudy solution formed. After 3 hr the thick reaction mixture was filtered, washed with 15 mL of hexane, and filtered again. Concentration gave a clear oil (quantitative weight recovery) that was used in the next step without any purification. A clear yellow solution formed immediately a white cloudy solution formed After 3 hr the thick reaction mixture was filtered washed with 15 mL of hexane filtered again Concentration gave a clear oil (quantitative weight recovery) that was used in the next step without any purification

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: According to the procedure as described in Example 1,2,2-dimethyl-1-methoxy-3-[(ethyldimethylsilyl)oxy]propane was prepared from intermediate 2,2-dimethyl-3-methoxy-1-propanol and reagent ethyldimethylsilyl chloride.