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

Temperature

0 °C

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.

1. customUpon completion of the reaction
2. customthe reaction was terminated
3. additionby adding 77 μL of water, 154 μL of 10% aqueous sodium hydroxide solution and 231 μL of water in order
4. customWhen the white viscous precipitate was produced
5. filtrationthe mixture was filtered through silica pad
6. customto remove the precipitate
7. concentrationThe resulting solution was concentrated by distillation under reduced pressure
8. custompurified by column chromatography

ORD record

ord-d5ba5238ed624b6684e82be77b24e065

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809012B2