Reaction #70207

Reaction equation

3′-Isopropoxy-4′-methoxyacetophenone

compound 19

O-(4-Nitrobenzyl)hydroxylamine Hydrochloride

→

CP30254

Yield 89.0%

(E)-3′-Isopropoxy-4′-methoxyacetophenone O-4-Nitrobenzyl Oxime

Yield 89.0%

Conditions

Workup

1. 1
   TemperatureAfter being heated for 3 h the reaction mixture
2. 2
   Temperaturewas cooled
3. 3
   Otherthe solvent removed under reduced pressure
4. 4
   workup.DISSOLUTIONThe ensuing yellow oil was dissolved in CH2Cl2 (20 mL)
5. 5
   Washthe resulting solution washed with H2O (2×15 mL)
6. 6
   Dryingthen dried (MgSO4)
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated under reduced pressure
9. 9
   OtherThe oil thus obtained
10. 10
    Washwas subjected to flash chromatography (15:85 v/v ethyl acetate/hexane elution)

Procedure

3′-Isopropoxy-4′-methoxyacetophenone (8) (150 mg, 0.720 mmol) was condensed with compound 19 (162 mg, 0.792 mmol) according to the general procedure II-A defined above. After being heated for 3 h the reaction mixture was cooled and the solvent removed under reduced pressure. The ensuing yellow oil was dissolved in CH2Cl2 (20 mL) and the resulting solution washed with H2O (2×15 mL) then dried (MgSO4), filtered and concentrated under reduced pressure. The oil thus obtained was subjected to flash chromatography (15:85 v/v ethyl acetate/hexane elution) to afford the title compound CP30254 (229 mg, 89%) as a pale-yellow oil, which solidified upon extensive standing, m.p. 44.5-46.1° C., Rf 0.5 in 1:1 v/v ethyl acetate/hexane.

Source