반응 #2329972

반응 방정식

potassium tert-butoxide

phenylacetonitrile

(2-bromoethoxy)trimethyl-silane

→

2-phenyl-4-trimethylsilanyloxy-butyronitrile

용매

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONUpon completion of the addition
2. 2
   온도the reaction mixture was refluxed for 5 h
3. 3
   기타quenched
4. 4
   workup.ADDITIONby pouring onto a mixture of ice and water
5. 5
   기타The formed organic phase was separated
6. 6
   추출the aqueous phase was extracted with benzene
7. 7
   세척The combined organic phases were washed with water
8. 8
   건조dried over magnesium sulfate
9. 9
   여과filtered
10. 10
    농축concentrated on a rotary evaporator

실험 절차

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.

출처