反应详情

To a solution of 8.73 ml of oxalyl chloride in 90 ml of methylene chloride is dropwise added 14.2 ml of dimethyl sulfoxide at -70° C. over 30 minutes. The solution is stirred at the same temperature for ten minutes, after which a solution of 11 g of 2-(2-chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanol in 90 ml of methylene chloride is dropwise added thereto at the same temperature over 30 minutes. The resulting mixture is stirred at the same temperature for 30 minutes, and then, 50.2 ml of triethylamine is dropwise added thereto. The temperature of the resulting mixture is elevated to room temperature, and thereafter, 200 ml of diethyl ether is added thereto. Then, insolubles are removed from the diethyl ether-added mixture by filtration. Then, the solvent is removed from the resulting filtrate by distillation under reduced pressure. To the residue obtained are added 200 ml of water and 200 ml of ethyl acetate, and then, the pH is adjusted to 1 with 1 N hydrochloric acid. Thereafter, the resulting organic layer is separated, washed successively with water and a saturated saline solution and then dried over anhydrous magnesium sulfate. The solvent is removed from the thus dried layer by distillation under reduced pressure. To the residue obtained is added 50 ml of diethyl ether, after which insolubles are collected by filtration, to obtain 9.5 g of colorless, solid 2-(2-chloroethoxy)-1-(6-fluorobenzo[b]thiophen-5-yl)ethanone.

1. customat -70° C.
2. customover 30 minutes
3. stirringThe resulting mixture is stirred at the same temperature for 30 minutes
4. customis elevated to room temperature
5. customThen, insolubles are removed from the diethyl ether-
6. additionadded mixture
7. filtrationby filtration
8. customThen, the solvent is removed from the resulting filtrate by distillation under reduced pressure
9. customTo the residue obtained
10. customThereafter, the resulting organic layer is separated
11. washwashed successively with water
12. dry with materiala saturated saline solution and then dried over anhydrous magnesium sulfate
13. customThe solvent is removed from the thus dried layer by distillation under reduced pressure
14. customTo the residue obtained
15. filtrationafter which insolubles are collected by filtration