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

Temperatur

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 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.

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
4. customWhen the white viscous precipitate was produced
5. filtrationthe mixture was filtered through a silica pad
6. customto remove the precipitate
7. concentrationThe resulting solution was concentrated by distillation under reduced pressure
8. custompurified by column chromatography

ORD-Eintrag

ord-19996c85b8074865ab2da9e5ac55d734

Quelldatensatz

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08809012B2