[4-(2-trimethylsilylethynyl)phenyl]methanol

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

Procedure: Under argon condition, 4-((trimethylsilyl)ethynyl)benzoic acid methyl ester (316 mg, 1.36 mmol) was dissolved in 5 mL of dry THF, and then cooled to 0° C., and LiAlH4 (2.04 mL, 1.0 M solution in THF, 2.04 mmol) was slowly added thereto. Upon completion of the reaction after stirring for 30 minutes at 0° C., the reaction was terminated by adding 77 μL of water, 154 μL of 10% aqueous sodium hydroxide solution and then 231 μL of water. When the white viscous precipitate was produced, the mixture was filtered through a silica pad to remove the precipitate. The resulting solution was concentrated by distillation under reduced pressure, and purified by column chromatography to obtain 258 mg (1.26 mmol, 93%) of the desired compound. Upon completion of the reaction the reaction was terminated by adding 77 μL of water, 154 μL of 10% aqueous sodium hydroxide solution When the white viscous precipitate was produced the mixture was filtered through a silica pad to remove the precipitate The resulting solution was concentrated by distillation under reduced pressure purified by column chromatography

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

Procedure: Under argon condition, (4-((trimethylsilyl)ethynyl)phenyl) methanol (258 mg, 1.26 mmol) was dissolved in 5 mL of dry THF and then cooled to 0° C., and imidazole (103 mg, 1.52 mmol) and TBSCl (228 mg, 1.52 mmol) dissolved in 3 mL of dry THF were added thereto. Thereafter, the temperature was raised to room temperature, and the reaction mixture was stirred for 15 hours at room temperature. Upon completion of the reaction, the reaction was terminated by adding 10 mL of aqueous saturated ammonium chloride solution. The reaction mixture was extracted with ethyl acetate (10 mL×4), and the organic layer thus obtained was treated with anhydrous magnesium sulfate to remove water. The precipitate was filtered out and the resulting solution was concentrated by distillation under reduced pressure, and purified by column chromatography to obtain 383 mg (1.20 mmol, 95%) of the desired compound. were added Thereafter, the temperature was raised to room temperature Upon completion of the reaction the reaction was terminated by adding 10 mL of aqueous saturated ammonium chloride solution The reaction mixture was extracted with ethyl acetate (10 mL×4) the organic layer thus obtained to remove water The precipitate was filtered out the resulting solution was concentrated by distillation under reduced pressure purified by column chromatography

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

Procedure: Under argon condition, 4-((trimethylsilyl)ethynyl)benzoic acid methyl ester (316 mg, 1.36 mmol) was dissolved in 5 mL of dry THF and then cooled to 0° C. and LiAlH4 (2.04 mL, 1.0 M solution in THF, 2.04 mmol) was slowly added thereto. Upon completion of the reaction after stirring for 30 minutes at 0° C., the reaction was terminated by adding 77 μL of water, 154 μL of 10% aqueous sodium hydroxide solution and 231 μL of water in order. When the white viscous precipitate was produced, the mixture was filtered through silica pad to remove the precipitate. The resulting solution was concentrated by distillation under reduced pressure, and purified by column chromatography to obtain 258 mg (1.26 mmol, 93%) of the desired compound. Upon completion of the reaction the reaction was terminated by adding 77 μL of water, 154 μL of 10% aqueous sodium hydroxide solution and 231 μL of water in order When the white viscous precipitate was produced the mixture was filtered through silica pad to remove the precipitate The resulting solution was concentrated by distillation under reduced pressure purified by column chromatography

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

Procedure: Under argon condition, (4-((trimethylsilyl)ethynyl)phenyl) methanol (258 mg, 1.26 mmol) was dissolved in 5 mL of dry THF and then cooled to 0° C., and imidazole (103 mg, 1.52 mmol) and TBSCl (228 mg, 1.52 mmol) dissolved in 3 mL of dry THF were added thereto. Thereafter, the temperature was raised to room temperature, and the reaction mixture was stirred for 15 hours at room temperature. Upon completion of the reaction, the reaction was terminated by adding 10 mL of aqueous saturated ammonium chloride solution. The reaction mixture was extracted with ethyl acetate (10 mL×4), and the organic layer thus obtained was treated with anhydrous magnesium sulfate to remove water. The precipitate was filtered out and the resulting solution was concentrated by distillation under reduced pressure, and purified by column chromatography to obtain 383 mg (1.20 mmol, 95%) of the desired compound. were added Thereafter, the temperature was raised to room temperature Upon completion of the reaction the reaction was terminated by adding 10 mL of aqueous saturated ammonium chloride solution The reaction mixture was extracted with ethyl acetate (10 mL×4) the organic layer thus obtained to remove water The precipitate was filtered out the resulting solution was concentrated by distillation under reduced pressure purified by column chromatography

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

Procedure: Under argon condition, 4-((trimethylsilyl)ethynyl)benzoic acid methyl ester (316 mg, 1.36 mmol) was dissolved in 5 mL of dry THF and then cooled to 0° C. and LiAlH4 (2.04 mL, 1.0 M solution in THF, 2.04 mmol) was slowly added thereto. Upon completion of the reaction after stirring for 30 minutes at 0° C., the reaction was terminated by adding 77 μL of water, 154 μL of 10% aqueous sodium hydroxide solution and 231 μL of water in order. When the white viscous precipitate was produced, the mixture was filtered through silica pad to remove the precipitate. The resulting solution was concentrated by distillation under reduced pressure, and purified by column chromatography to obtain 258 mg (1.26 mmol, 93%) of the desired compound. Upon completion of the reaction the reaction was terminated by adding 77 μL of water, 154 μL of 10% aqueous sodium hydroxide solution and 231 μL of water in order When the white viscous precipitate was produced the mixture was filtered through silica pad to remove the precipitate The resulting solution was concentrated by distillation under reduced pressure purified by column chromatography