Reacción #2329972

Ecuación de reacción

potassium tert-butoxide

phenylacetonitrile

(2-bromoethoxy)trimethyl-silane

→

2-phenyl-4-trimethylsilanyloxy-butyronitrile

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONUpon completion of the addition
2. 2
   Temperaturathe reaction mixture was refluxed for 5 h
3. 3
   Otroquenched
4. 4
   workup.ADDITIONby pouring onto a mixture of ice and water
5. 5
   OtroThe formed organic phase was separated
6. 6
   Extracciónthe aqueous phase was extracted with benzene
7. 7
   LavadoThe combined organic phases were washed with water
8. 8
   Secadodried over magnesium sulfate
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated on a rotary evaporator

Procedimiento

A suspension of potassium tert-butoxide (12.3 g) in toluene (200 mL) was treated dropwise with a mixture of phenylacetonitrile (12.9 g) and (2-bromoethoxy)trimethyl-silane (23.8 g) at room temperature. Upon completion of the addition, the reaction mixture was refluxed for 5 h, then cooled to room temperature and quenched by pouring onto a mixture of ice and water. The formed organic phase was separated and the aqueous phase was extracted with benzene. The combined organic phases were washed with water, dried over magnesium sulfate, filtered and concentrated on a rotary evaporator to give 2-phenyl-4-trimethylsilanyloxy-butyronitrile. The obtained butyronitrile derivative was redissolved in a mixture of ethanol (40 mL) and 70% aqueous sulfuric acid (40 mL), stirred at 50° C. for 3 h and, after cooling to room temperature, diluted with water (150 mL). The resulted organic phase was separated and the aqueous phase was extracted with benzene. The combined organic phases were washed with water, then with saturated aqueous solution of sodium bicarbonate, dried over magnesium sulfate, filtered, concentrated on a rotary evaporator and distilled in vacuum to give 11.0 g (62%) of the title compound.

Fuente