Methyl 4-trimethylsilylethynylbenzoate → 4-(Trimethylsilylethynyl)benzyl alcohol

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence