Reaktion #45756

Reaktionsgleichung

diisopropylethylamine

ethyl azetidine-3-acetate

2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile

→

compound

Ausbeute 76.3%

Ethyl [1-(4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazol-2-yl)azetidin-3-yl]acetate

Ausbeute 76.3%

Lösungsmittel

methylene chloride

chloroform

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturby heating
3. 3
   Temperaturunder reflux for 19 hours
4. 4
   TemperaturAfter cooling
5. 5
   Waschenwashing with water
6. 6
   Trocknenthe organic layer was dried over anhydrous magnesium sulfate
7. 7
   Sonstigethe solvent was evaporated away under reduced pressure

Vorschrift

Under nitrogen atmosphere, 2-chloro-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-4-cabonitrile (I-130) (400 mg, 1.40 mmol) was dissolved in methylene chloride (15 ml), then diisopropylethylamine (537 μl, 3.08 mmol) and ethyl azetidine-3-acetate (503 mg, 2.80 mmol) dissolved in methylene chloride (5 ml) were added, followed by heating under reflux for 19 hours. After cooling, diluting with chloroform and washing with water, the organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated away under reduced pressure. The resulting residue was subjected to preparative silica gel column chromatography. From the eluate with ethyl acetate/hexane (1:1, v/v), the entitled compound (420 mg, 76%) was obtained as a colorless oil.

Quelle