Reacción #835971

Ecuación de reacción

ethyl acetate

2-buten-1,4-diol

imidazole

t-butylchlorodiphenylsilane

→

title compound

Rendimiento 42.0%

4-(t-Butyldiphenylsilyloxy)-2-buten-1-ol

Rendimiento 42.0%

Disolventes

dichloromethane N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter completion of the dropwise addition
2. 2
   OtroThe residue obtained
3. 3
   Concentraciónby concentrating the reaction mixture under reduced pressure
4. 4
   workup.ADDITIONwas added with diethyl ether
5. 5
   FiltraciónFrom the resulting mixture, the insoluble matter was filtered off
6. 6
   LavadoThe diethyl ether layer was washed with water
7. 7
   Secadothe organic layer was dried over anhydrous magnesium sulfate
8. 8
   ConcentraciónAfter fitration, the filtrate was concentrated under reduced pressure
9. 9
   Otrothe fraction obtained from the hexane

Procedimiento

In a dichloromethane/N,N-dimethylformamide (200 ml/200 ml) mixture were dissolved 2-buten-1,4-diol (10.0 g, 113 mmol) and imidazole (4.70 g, 69.0 mmol), followed by the dropwise addition of t-butylchlorodiphenylsilane (30.0 ml, 115 mmol) at room temperature. After completion of the dropwise addition, the mixture was stirred at room temperature for 4 days. The residue obtained by concentrating the reaction mixture under reduced pressure was added with diethyl ether. From the resulting mixture, the insoluble matter was filtered off. The diethyl ether layer was washed with water and then, the organic layer was dried over anhydrous magnesium sulfate. After fitration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=2:1 eluate was concentrated under reduced pressure, whereby the title compound (15.3 g, 46.9 mmol, 42%) was obtained as a colorless oil.

Fuente