반응 #6493

반응 방정식

1-cyano-6-methoxy-3,4-dihydronaphthalene

product

1-Cyano-6-methoxy-3,4-dihydronaphthalene

diisopropylamine

n-butyllithium

acetonitrile

→

title compound

수율 74.2%

1-Cyano-2-(cyanomethyl)-6-methoxy-1,2,3,4-tetrahydronaphthalene

수율 74.2%

용매

THF

THF

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONTo the stirred solution was added, dropwise over a 25 minute period
2. 2
   workup.STIRRINGThe solution was stirred for 20 min at -78° C.
3. 3
   온도to warm to ambient temperature
4. 4
   workup.STIRRINGwas stirred at ambient temperature for 1 h
5. 5
   기타the reaction was quenched
6. 6
   workup.ADDITIONby pouring the reaction mixture into and then the reaction
7. 7
   기타was quenched
8. 8
   workup.ADDITIONby pouring the reaction mixture into saturated aqueous ammonium chloride solution
9. 9
   기타The layers were separated
10. 10
    추출the aqueous layer was extracted with ethyl acetate
11. 11
    건조The combined organic layers were dried over anhydrous magnesium sulfate
12. 12
    여과filtered
13. 13
    농축concentrated in vacuo
14. 14
    기타The residue was purified by chromatography on silica gel
15. 15
    세척eluted with 25% ethyl acetate in hexane

실험 절차

To a solution of 1.05 mL (7.5 mmol) of diisopropylamine in 10 mL of THF at -78° C., under a nitrogen atmosphere, was added n-butyllithium (2.2 mL of a 2.5M solution in THF, 5.5 mmol) and the resultant solution was stirred at -78° C. for 40 min. To the stirred solution was added, dropwise over a 25 minute period, a solution of 274 μL (5.25 mmol) of acetonitrile in 5 mL of THF. The solution was stirred for 20 min at -78° C. and then a solution of 926 mg (5 mmol) of 1-cyano-6-methoxy-3,4-dihydronaphthalene (the product of Step 2 of Example 1) in 5 mL of THF was added via syringe pump over a 20 min period. The reaction mixture then allowed to warm to ambient temperature and was stirred at ambient temperature for 1 h and then the reaction was quenched by pouring the reaction mixture into 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. The residue was purified by chromatography on silica gel eluted with 25% ethyl acetate in hexane to give 840 mg (74% yield) of the title compound as a 1:1 mixture of the cis and trans isomers; MS DCl--NH3M/Z: 244 (M+H)+.

출처