반응 #42977
ord-1e9863cb42ed4921b0a3592741db4058
반응 방정식
반응물
시약
반응 조건
후처리
- 1기타A dry 3 L three-necked, round-bottomed flask was fitted with a magnetic stirring bar
- 2온도the flask was cooled with an ice bath
- 3기타the layers were separated
- 4추출The aqueous layer was extracted with three 400 mL portions of ethyl acetate
- 5세척washed successively with 1 IL of saturated aqueous sodium bicarbonate and 1 L of saturated aqueous sodium chloride
- 6건조The organic solution was dried with anhydrous magnesium sulfate
- 7여과filtered
- 8기타evaporated (aspirator vacuum, ca. 30° C.)
- 9기타The oily residue was chromatographed on 800 g
- 10세척of Silica gel 60 by eluting with 5:1-1:1 (v/v) hexane-ethyl acetate mixture
- 11세척The elution
- 12기타was evaporated
실험 절차
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.