Réaction #167310

Équation de réaction

1-[4-Fluoro-3-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

NaH

MeOH

→

product

Rendement 14.5%

1-(3-Methyl-benzo[d]isoxazol-5-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

Rendement 14.5%

Solvants

CHCl3

DMF

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was partitioned between ethylacetate and ice water
2. 2
   LavageThe organic layer was washed with brine solution
3. 3
   Séchagedried over Na2SO4
4. 4
   Concentrationconcentrated
5. 5
   AutrePurification by column chromatography on silica gel (1% MeOH in CHCl3)

Mode opératoire

1-[4-Fluoro-3-(1-hydroxyimino-ethyl)-phenyl]-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (220 mg, 0.670 mmol) in DMF (5 mL) was added to a stirred mixture of NaH (19 mg, 0.804 mmol) in DMF (2 mL) under nitrogen atmosphere at 0° C. The resulting mixture was stirred at room temperature for 21 hours. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ethylacetate and ice water. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (1% MeOH in CHCl3) afforded 28 mg of the product (14.5% yield).

Source