Reaction #70216

Reaction equation

Acetophenone

3′-Hydroxy-4′-methoxyacetophenone

O-(2-fluorobenzyl)hydroxylamine hydrochloride

→

CP30280

Yield 91.0%

(E)-3′-Hydroxy-4′-methoxyacetophenone O-2-Fluorobenzyl Oxime

Yield 91.0%

Solvents

ethyl acetate hexane

ethyl acetate hexane

Conditions

Workup

1. 1
   TemperatureAfter being heated for 36 h the reaction mixture
2. 2
   Temperaturewas cooled
3. 3
   Otherthe solvent removed under reduced pressure
4. 4
   workup.DISSOLUTIONThe ensuing residue was dissolved in CH2Cl2 (15 mL)
5. 5
   Washthe resulting solution washed with H2O (2×10 mL)
6. 6
   Dryingthen dried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   OtherThe oil thus obtained

Procedure

Acetophenone 12 (50 mg, 0.301 mmol) was condensed with O-(2-fluorobenzyl)hydroxylamine hydrochloride (32) (58 mg, 0.327 mmol) according to the general procedure II-B defined above. After being heated for 36 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) to afford the title compound CP30280 (79 mg, 91%) as a pale-yellow oil, Rf 0.5 in 1:1 v/v ethyl acetate/hexane.

Source