반응 #1694586

반응 방정식

4-phenylbutyl bromide

sodium hydride

diisopropylamine

1-naphthoxyacetic acid

n-butyllithium

hexane

→

(±)-2-(1-naphthoxy)-6-phenylhexanoic acid

수율 23.6%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도cooling
2. 2
   온도heated
3. 3
   온도under reflux for 15 minutes
4. 4
   온도After cooling below 5° C., to the reaction mixture
5. 5
   workup.STIRRINGwas stirred below 10° C. for 20 minutes
6. 6
   온도warmed for 20 minutes at 30° C
7. 7
   온도After cooling below 5° C. again
8. 8
   workup.STIRRINGThe mixture was stirred for 30 minutes at below 5° C.
9. 9
   온도warmed for 1 hour at 30° C.
10. 10
    workup.STIRRINGwith stirring
11. 11
    온도After cooling
12. 12
    세척the reaction mixture was washed with diethyl ether
13. 13
    기타to remove neutral materials
14. 14
    workup.ADDITIONby adding concentrated hydrochloric acid
15. 15
    추출extracted with ethyl acetate
16. 16
    세척The organic layer was washed with a saturated sodium chloride aqueous solution
17. 17
    건조dried over anhydrous magnesium sulfate
18. 18
    농축concentrated under reduced pressure
19. 19
    기타The residue was purified by silica gel flash column chromatography (eluent: benzene)

실험 절차

To a mixture of 5 ml of dry tetrahydrofuran and 0.26 g of 50% sodium hydride (suspension in oil) were added 0.7 ml of diisopropylamine and 1.0 g of 1-naphthoxyacetic acid with stirring under an argon atmosphere under ice-cooling. The mixture was heated for 30 minutes at 50° C., and then heated under reflux for 15 minutes. After cooling below 5° C., to the reaction mixture was added dropwise 3.5 ml of n-butyllithium (as a 1.6 mole hexane solution), the mixture was stirred below 10° C. for 20 minutes, and then warmed for 20 minutes at 30° C. After cooling below 5° C. again, 1.00 g of 4-phenylbutyl bromide was added to the reaction mixture. The mixture was stirred for 30 minutes at below 5° C., and then warmed for 1 hour at 30° C. with stirring. After cooling, the reaction mixture was washed with diethyl ether to remove neutral materials. The aqueous layer was acidified by adding concentrated hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (eluent: benzene) to obtain 0.37 g of (±)-2-(1-naphthoxy)-6-phenylhexanoic acid as colorless crystals.

출처