Reacción #164506

Ecuación de reacción

2-hydroxyacetophenone

triethylamine

tert-butyldimethylsilyl chloride

→

title compound

Rendimiento 70.7%

2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-ethanone

Rendimiento 70.7%

Disolventes

dichloromethane

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with 10% citric acid
2. 2
   Concentraciónsaturate sodium carbonate, brine
3. 3
   Secadodried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   OtroThe residue is purified via silica gel chromatography (20% ethyl acetate in hexanes)

Procedimiento

To a well stirred solution of 2-hydroxyacetophenone (1.0 g, 7.34 mmol) in dichloromethane (15 mL) is added triethylamine (1.23 mL, 8.81 mmol), 4-dimethylaminopyridine (45 mg, 0.367 mmol) and tert-butyldimethylsilyl chloride (1.16 g, 7.71 mmol) dissolved in dichloromethane (2 mL). The reaction mixture is stirred at room temperature for 1 h, then diluted with dichloromethane (50 mL), washed with 10% citric acid, saturate sodium carbonate, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified via silica gel chromatography (20% ethyl acetate in hexanes) to yield the title compound as a yellow oil (1.3 g, 5.19 mmol).

Fuente