تفاعل #6076

معادلة التفاعل

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

المذيبات

DMF

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىThe resulting reaction mixture
2. 2
   workup.STIRRINGthe reaction mixture is stirred at r.t. for 3 hrs
3. 3
   أخرى, the solvent evaporated in vacuo
4. 4
   درجة الحرارةcooled water
5. 5
   استخلاصextracted with ethyl acetate
6. 6
   تجفيفThe collected organic phases are dried over Na2SO4
7. 7
   أخرىevaporated
8. 8
   أخرىto give an oily crude material which
9. 9
   أخرىis chromatographed over silica gel
10. 10
    غسيلBy eluting with CH2Cl2 /MeOH (95:5)

الإجراء التجريبي

(+-)-(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.

المصدر