Reacción #70215

Ecuación de reacción

Acetophenone

3′-Hydroxy-4′-methoxyacetophenone

O-(4-fluorobenzyl)hydroxylamine hydrochloride

→

CP30266

Rendimiento 80.4%

(E)-3′-Hydroxy-4′-methoxyacetophenone O-4-Fluorobenzyl Oxime

Rendimiento 80.4%

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter being heated for 24 h the reaction mixture
2. 2
   Temperaturawas cooled
3. 3
   Otrothe solvent removed under reduced pressure
4. 4
   workup.DISSOLUTIONThe ensuing residue was dissolved in CH2Cl2 (15 mL)
5. 5
   Lavadothe resulting solution washed with H2O (2×10 mL)
6. 6
   Secadothen dried (MgSO4)
7. 7
   Filtraciónfiltered
8. 8
   Concentraciónconcentrated under reduced pressure
9. 9
   OtroThe oil thus obtained
10. 10
    Lavadowas subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution)

Procedimiento

Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(4-fluorobenzyl)hydroxylamine hydrochloride (29) (58 mg, 0.327 mmol) according to the general procedure II-B defined above. After being heated for 24 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing residue was dissolved in CH2Cl2 (15 mL) and the resulting solution washed with H2O (2×10 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution) to afford the title compound CP30266 (70 mg, 80%) as a pale-purple waxy-oil, Rf 0.5 in 1:1 v/v ethyl acetate/hexane.

Fuente