Reacción #2304277

Ecuación de reacción

water

2-methyl-5-(trimethylsilyl)phenoxytrimethylsilane

Intermediate 2

2-methyl-5-(trimethylsilyl)phenoxytrimethylsilane

tetrabutylammonium fluoride

→

title compound

Rendimiento 56.0%

5-Trimethylsilyl-2-methylphenol

Rendimiento 56.0%

Disolventes

diethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe mixture was extracted with diethyl ether (2×40 mL)
2. 2
   Secadothe combined organic extracts were dried (magnesium sulphate)
3. 3
   Concentraciónconcentrated under reduced pressure
4. 4
   Otropurified by column chromatography (SiO2; light petroleum to 9:1 light petroleum-diethyl ether)

Procedimiento

To a solution of 2-methyl-5-(trimethylsilyl)phenoxytrimethylsilane (Intermediate 2; 5 g) in diethyl ether (40 mL) at room temperature was added tetrabutylammonium fluoride (TBAF; 19.3 mL, 1.0 M solution, 19.3 mmol). The reaction was stirred at this temperature for 5 minutes and then water (40 mL) was added. The mixture was extracted with diethyl ether (2×40 mL) and the combined organic extracts were dried (magnesium sulphate), concentrated under reduced pressure and purified by column chromatography (SiO2; light petroleum to 9:1 light petroleum-diethyl ether) to give the title compound as a colourless oil (1.9 g, 56%). Rf=0.32 (9:1 light petroleum-diethyl ether). 1H NMR δH 0.26 (9 H, s), 2.27 (3 H, s), 4.62 (1 H, s), 6.93 (1 H, d, J=1.0 Hz), 7.02 (1 H, dd, J=7.3, 1.0 Hz), 7.15 (1 H, d, J=7.3 Hz).

Fuente