反応 #42977

反応方程式

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

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他A dry 3 L three-necked, round-bottomed flask was fitted with a magnetic stirring bar
2. 2
   温度the flask was cooled with an ice bath
3. 3
   その他the layers were separated
4. 4
   抽出The aqueous layer was extracted with three 400 mL portions of ethyl acetate
5. 5
   洗浄washed successively with 1 IL of saturated aqueous sodium bicarbonate and 1 L of saturated aqueous sodium chloride
6. 6
   乾燥The organic solution was dried with anhydrous magnesium sulfate
7. 7
   ろ過filtered
8. 8
   その他evaporated (aspirator vacuum, ca. 30° C.)
9. 9
   その他The oily residue was chromatographed on 800 g
10. 10
    洗浄of Silica gel 60 by eluting with 5:1-1:1 (v/v) hexane-ethyl acetate mixture
11. 11
    洗浄The elution
12. 12
    その他was evaporated

実験手順

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.

出典