Reacción #6076

Ecuación de reacción

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

Disolventes

DMF

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe resulting reaction mixture
2. 2
   workup.STIRRINGthe reaction mixture is stirred at r.t. for 3 hrs
3. 3
   Otro, the solvent evaporated in vacuo
4. 4
   Temperaturacooled water
5. 5
   Extracciónextracted with ethyl acetate
6. 6
   SecadoThe collected organic phases are dried over Na2SO4
7. 7
   Otroevaporated
8. 8
   Otroto give an oily crude material which
9. 9
   Otrois chromatographed over silica gel
10. 10
    LavadoBy eluting with CH2Cl2 /MeOH (95:5)

Procedimiento

(+-)-(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.

Fuente