반응 #727135

반응 방정식

Diethyl chlorophosphate

5-(4-ethylbenzyl)benzo[b]thiophene

n-butyllithium n-hexane

→

title compound

5-(4-Ethylbenzyl)benzo[b]thiophen-2-phosphonic acid diethylester

용매

THF

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction mixture was stirred for 0.5 hr at −78° C
2. 2
   기타The reaction was quenched by the addition of saturated aqueous ammonium chloride
3. 3
   추출extracted with ethyl acetate
4. 4
   세척The combined ethyl acetate extracts were washed with brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   기타evaporated
7. 7
   기타The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/2)

실험 절차

To a solution of 5-(4-ethylbenzyl)benzo[b]thiophene (1.50 g) in THF (11.8 mL) was added 2.44 M n-butyllithium/n-hexane solution (2.9 mL) at −78° C., and the reaction mixture was stirred for 1 hr at same temperature. Diethyl chlorophosphate (0.9 mL) was added to the reaction mixture at −78° C., and the reaction mixture was stirred for 0.5 hr at −78° C. The reaction was quenched by the addition of saturated aqueous ammonium chloride and extracted with ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane=1/2) to give the title compound (1.79 g) as a colorless oil.

출처