反应详情

A stirred chilled (-5° C.) solution of 2-(6,11-dihydro-11-oxodibenz[b,e]oxepin-2-yl)ethanol (5.08 g, 0.02 mol) and anhydrous pyridine (28 ml) was treated over 60 seconds with methanesulfonyl chloride (2.74 g, 0.024 mol). A mild exotherm was noted and a precipitate separated with continued cooling and stirring for 15 minutes after addition of the methanesulfonyl chloride was completed. Additional methanesulfonyl chloride (1.37 g, 0.012 mol) was added over 30 seconds and after stirring for 15 minutes the cooling bath was removed. After stirring 2 hours at ambient temperature, the mixture was decanted into 400 ml of ice cold water. The aqueous phase was decanted and the residual oil was stirred with water (300 ml). The water was decanted and the residual semisolid was triturated with ether. The resultant solid was collected, washed with ether and dried in vacuo to afford 4.92 g of crude material. Recrystallization from acetonitrile (15 ml) afforded 2.60 g (39.1 %) of crystals, m.p. 108°-110° C.

1. customa precipitate separated
2. temperaturewith continued cooling
3. additionafter addition of the methanesulfonyl chloride
4. stirringafter stirring for 15 minutes the cooling bath
5. customwas removed
6. stirringAfter stirring 2 hours at ambient temperature
7. customthe mixture was decanted into 400 ml of ice cold water
8. customThe aqueous phase was decanted
9. stirringthe residual oil was stirred with water (300 ml)
10. customThe water was decanted
11. customthe residual semisolid was triturated with ether
12. customThe resultant solid was collected
13. washwashed with ether
14. customdried in vacuo
15. customto afford 4.92 g of crude material
16. customRecrystallization from acetonitrile (15 ml)