반응 #2507822

반응 방정식

p-toluenesulfonyl cyanide

n-butyl-lithium

7-bromo-6,6′-difluoro-3′-propyl-3,4,3′,4′-tetrahydro-2H,2′H-[3,7′]bichromenyl

→

6,6′-difluoro-3′-propyl-3,4,3′,4′-tetrahydro-2H,2′H-[3,7]bichromenyl-7-carbonitrile

용매

ether

THF

hexane

THF

반응 조건

후처리

1. 1
   workup.WAITThe batch is left
2. 2
   기타does not exceed −65° C
3. 3
   workup.WAITAfter 30 min
4. 4
   세척washed with dil. hydrochloric acid
5. 5
   건조phase is dried over sodium sulfate
6. 6
   기타evaporated
7. 7
   기타the crude product is chromatographed on silica gel with heptane/toluene (2:3)

실험 절차

1.4 g (3.31 mmol) of 7-bromo-6,6′-difluoro-3′-propyl-3,4,3′,4′-tetrahydro-2H,2′H-[3,7′]bichromenyl are dissolved in 20 ml of THF, and 3 ml (4.8 mmol) of a 15 percent solution of n-butyl-lithium in hexane are added at −50° C. The batch is left to stir for 2 h at −70° C., and a solution of 0.9 g (5.00 mmol) of p-toluenesulfonyl cyanide in 10 ml of THF is subsequently added at such a rate that the temperature does not exceed −65° C. After 30 min, the batch is allowed to thaw, diluted with ether and washed with dil. hydrochloric acid. The org. phase is dried over sodium sulfate and evaporated, and the crude product is chromatographed on silica gel with heptane/toluene (2:3), giving 6,6′-difluoro-3′-propyl-3,4,3′,4′-tetrahydro-2H,2′H-[3,7]bichromenyl-7-carbonitrile as colourless crystals of m.p. 122° C.

출처