반응 #6076

반응 방정식

sodium hydride

ethyl-5-bromopentanoate

(+-)-(E)-2-(1H-imidazol-1-yl)-1,2,3,4-tetrahydronaphtalen-1-one oxime

pentane

→

title compound

(+-)-(E)-Ethyl-5-[[2-(1H-imidazol-1-yl)-1,2,3,4-tetrahydro-1-naphtylidene]aminoxy]pentanoate

용매

DMF

DMF

반응 조건

후처리

1. 1
   기타The resulting reaction mixture
2. 2
   workup.STIRRINGthe reaction mixture is stirred at r.t. for 3 hrs
3. 3
   기타, the solvent evaporated in vacuo
4. 4
   온도cooled water
5. 5
   추출extracted with ethyl acetate
6. 6
   건조The collected organic phases are dried over Na2SO4
7. 7
   기타evaporated
8. 8
   기타to give an oily crude material which
9. 9
   기타is chromatographed over silica gel
10. 10
    세척By eluting with CH2Cl2 /MeOH (95:5)

실험 절차

(+-)-(E)-2-(1H-imidazol-1-yl)-1,2,3,4-tetrahydronaphtalen-1-one oxime (500 mg; 2.2 mmoles) dissolved in dry DMF (27 ml) is added, under dry nitrogen atmosphere, to a pentane-washed sodium hydride suspension (160 mg NaH 55%; 3.6 mmoles), in dry DMF (10 ml). The resulting reaction mixture is stirred at r.t. for 2 hours. Then ethyl-5-bromopentanoate (0.530 ml; 3.3 mmoles) is added at r.t. and the reaction mixture is stirred at r.t. for 3 hrs., the solvent evaporated in vacuo, and the residue carefully taken up with ice-cooled water and extracted with ethyl acetate. The collected organic phases are dried over Na2SO4 and evaporated to give an oily crude material which is chromatographed over silica gel. By eluting with CH2Cl2 /MeOH (95:5), the pure title compound is obtained as a slight yellow oil (250 mg). 1H-NMR (200MH2, CDCl3) ppm.

출처