반응 #563923

반응 방정식

2-fluoronitrobenzene

4-hydroxytetrahydrothiopyran

sodium hydride

→

2-(tetrahydro-4H-thiopyran-4-yloxy)nitrobenzene

수율 83.7%

용매

dioxane

dioxane

반응 조건

후처리

1. 1
   workup.STIRRINGwith stirring for 6 hours
2. 2
   기타was returned to room temperature
3. 3
   workup.STIRRINGthe mixture was stirred overnight
4. 4
   추출extracted with ethyl ether
5. 5
   세척the ethyl ether layer was washed, in turn, with water
6. 6
   건조a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
7. 7
   기타The solvent was evaporated
8. 8
   기타1.1 g of the resulting oil was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=10:1 )

실험 절차

To 50 ml of a dioxane suspension containing 0.96 g of 60% sodium hydride was added 3.6 g of 4-hydroxytetrahydrothiopyran at room temperature, and the mixture was stirred on heating at 90° C. with stirring for 6 hours. The temperature of the mixture was returned to room temperature, then 10 ml of a dioxane solution of 4.5 g of 2-fluoronitrobenzene was added dropwise, and the mixture was stirred overnight. The reaction solution was poured into ice water and extracted with ethyl ether, and the ethyl ether layer was washed, in turn, with water and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was evaporated, and 1.1 g of the resulting oil was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=10:1 ) to give 6.1 g of 2-(tetrahydro-4H-thiopyran-4-yloxy)nitrobenzene as a pale yellow oil.

출처