반응 #6492

반응 방정식

3-phenylpropiononitrile

1-cyano-3,4-dihydronaphthalene

product

1-Cyano-3,4-dihydronaphthalene

diisopropylamine

n-butyllithium

→

title compound

수율 99.5%

1-Cyano-2-(1-cyano-2-phenyl-1-ethyl)-1,2,3,4-tetrahydronaphthalene

수율 99.5%

용매

THF

THF

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction mixture was stirred for 45 min at -78° C.
2. 2
   workup.STIRRINGThe reaction mixture was stirred at -78° C. for 0.5 h
3. 3
   기타the reaction was quenched
4. 4
   workup.ADDITIONby pouring the reaction mixture into saturated aqueous ammonium chloride solution
5. 5
   기타The layers were separated
6. 6
   추출the aqueous layer was extracted with ethyl acetate
7. 7
   건조The combined organic layers were dried over anhydrous magnesium sulfate
8. 8
   여과filtered
9. 9
   농축concentrated in vacuo

실험 절차

To a solution of 3.5 mL (25 mmol) of diisopropylamine in 40 mL of THF at -78° C., under a nitrogen atmosphere, was added n-butyllithium (9.5 mL of a 2.5M solution in THF, 23.7 mmol) and the resultant solution was stirred at -78° C. for 0.5 h. To the stirred solution was slowly added a solution of 2.75 g (21 mmol) of 3-phenylpropiononitrile in 40 mL of THF. The reaction mixture was stirred for 45 min at -78° C. and then a solution of 3.1 g (20 mmol) of 1-cyano-3,4-dihydronaphthalene (the product of Step 1 of Example 9) in 40 mL of THF was added. The reaction mixture was stirred at -78° C. for 0.5 h and then the reaction was quenched by pouring the reaction mixture into saturated aqueous ammonium chloride solution. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give 5.70 g (quantitative yield) of the title compound as a mixture of three diastereomers; MS DCl--NH3M/Z: 287 (M+H)+.

출처