Reaktion #453505

Reaktionsgleichung

3-(4-chloro-6-fluoro-2-formylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil

methyl magnesium bromide

water

→

desired product

Ausbeute 55.3%

3-[4-chloro-6-fluoro-2-(1-hydroxyethyl)benzofuran-7-yl]-1-methyl-6-trifluoromethyluracil

Ausbeute 55.3%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat -65° C
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed sequentially with water
4. 4
   Trocknena saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
6. 6
   SonstigeThen, the obtained residue was purified by silica gel column chromatography

Vorschrift

4.0 g (10.2 mmol) of 3-(4-chloro-6-fluoro-2-formylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 20 ml of tetrahydrofuran, and 12.3 ml of methyl magnesium bromide (1.0M tetrahydrofuran solution) was dropwise added thereto at -65° C. After stirring at room temperature for 1 hour, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 2.3 g (yield: 55.3%) of the desired product as pale yellow crystals. Melting point: 154-157° C.

Quelle