반응 #358978

반응 방정식

ammonium chloride

4-phenyl-6-methyl-1,2,3,5-tetrahydro-s-indacene

n-butyllithium

chloro-(2-i-propyl-4-phenyl-indenyl)-dimethylsilane

→

crude product

수율 104.3%

Dimethyl-(4-phenyl-6-methyl-1,2,3,5-tetrahydro-s-indacenyl)(2-i-propyl-4-phenyl-1-indenyl)-silane

수율 104.3%

용매

n-hexane

diethylether

반응 조건

후처리

1. 1
   workup.ADDITIONThen to the solution was added at −70° C
2. 2
   workup.STIRRINGstirred for 5 hrs
3. 3
   세척the organic layer was washed with brine
4. 4
   건조dried over sodium sulfate
5. 5
   기타the solvents were evaporated

실험 절차

To 12.3 g (50 mmol) of 4-phenyl-6-methyl-1,2,3,5-tetrahydro-s-indacene (2b) and 150 mg (1.5 mmol) of copper cyanide (I) in 450 ml of diethylether was added dropwise at −70° C. 23 ml (57 mmol) of 2.5 M of n-butyllithium in n-hexane. The solution was slowly warmed to room temperature and stirred for 3 hrs at room temperature. Then to the solution was added at −70° C. 16.4 g (50 mmol) of chloro-(2-i-propyl-4-phenyl-indenyl)-dimethylsilane and the solution was warmed to room temperature and stirred for 5 hrs. The resulting back slurry solution was poured into an aqueous ammonium chloride solution and the organic layer was washed with brine, dried over sodium sulfate and the solvents were evaporated to give 28 g of crude product. This was purified by column chromatography (800 g of silica gel, 101 Heptane:CH2Cl2=5:1). Yield: 9.5 g (35%)

출처