Reacción #42977

Ecuación de reacción

aluminum chloride

5-(3-Bromopropylidene)-5,11-dihydro[1]benzoxepino[2,3-b]pyridine

acetyl chloride

→

titled compound

7-Acetyl-5-(3-bromopropylidene)-5,11-dihydro[1]benzoxepino[2,3-b]pyridine

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA dry 3 L three-necked, round-bottomed flask was fitted with a magnetic stirring bar
2. 2
   Temperaturathe flask was cooled with an ice bath
3. 3
   Otrothe layers were separated
4. 4
   ExtracciónThe aqueous layer was extracted with three 400 mL portions of ethyl acetate
5. 5
   Lavadowashed successively with 1 IL of saturated aqueous sodium bicarbonate and 1 L of saturated aqueous sodium chloride
6. 6
   SecadoThe organic solution was dried with anhydrous magnesium sulfate
7. 7
   Filtraciónfiltered
8. 8
   Otroevaporated (aspirator vacuum, ca. 30° C.)
9. 9
   OtroThe oily residue was chromatographed on 800 g
10. 10
    Lavadoof Silica gel 60 by eluting with 5:1-1:1 (v/v) hexane-ethyl acetate mixture
11. 11
    LavadoThe elution
12. 12
    Otrowas evaporated

Procedimiento

A dry 3 L three-necked, round-bottomed flask was fitted with a magnetic stirring bar, a glass stopper, a rubber septum, and an argon inlet. Under an argon atmosphere, 94.0 g. of 5-(3-Bromopropylidene)-5,11-dihydro[1]benzoxepino[2,3-b]pyridine (0.30 mole) and 900 mL of dry dichloromethane were added to the flask and the flask was cooled with an ice bath. To the solution was slowly added 78.5 g. of aluminum chloride (0.83 mole), followed by 17.8 mL of acetyl chloride (0.25 mole), and the mixture was stirred for an hour at 0° C. The reaction mixture was poured to 1500 g of ice, and the layers were separated. The aqueous layer was extracted with three 400 mL portions of ethyl acetate. Dichloromethane layer and the organic extracts were combined and washed successively with 1 IL of saturated aqueous sodium bicarbonate and 1 L of saturated aqueous sodium chloride. The organic solution was dried with anhydrous magnesium sulfate, filtered, and evaporated (aspirator vacuum, ca. 30° C.). The oily residue was chromatographed on 800 g. of Silica gel 60 by eluting with 5:1-1:1 (v/v) hexane-ethyl acetate mixture. The elution was evaporated, giving the titled compound as a pale yellow solid.

Fuente