反应 #1726690

反应方程式

4A

(3-Hydroxyazetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone

Triethylamine

methanesulfonyl chloride

→

4B

收率 177.9%

1-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yl methanesulfonate

收率 177.9%

溶剂

dichloromethane

反应条件

后处理

1. 1
   温度was cooled in an ice-bath
2. 2
   workup.ADDITIONAfter the addition
3. 3
   其他the cooling bath was removed
4. 4
   其他The mixture was transferred to a separatory funnel
5. 5
   洗涤was washed with water
6. 6
   其他The organic solution was dried (phase separator)
7. 7
   其他evaporated
8. 8
   workup.ADDITIONDichloromethane (50 mL) and diethyl ether (200 mL) were added
9. 9
   过滤the solid product was filtered
10. 10
    洗涤The product was washed twice with diethyl ether
11. 11
    其他dried in vacuo

实验过程

A suspension of 4A (5.45 g, 19. 8 mmol) in dichloromethane (100 mL) was cooled in an ice-bath. Triethylamine (4.4 mL, 31.7 mmol) was added followed by methanesulfonyl chloride (2.3 mL, 29.7 mmol). After the addition, the cooling bath was removed. The mixture was stirred for 7 h. The mixture was transferred to a separatory funnel and was washed with water followed by aqueous NaHCO3 (sat.). The organic solution was dried (phase separator) and evaporated. Dichloromethane (50 mL) and diethyl ether (200 mL) were added and the solid product was filtered. The product was washed twice with diethyl ether and then dried in vacuo. There was obtained 5.03 g (72%) of 4B as a solid. 1H NMR (500 MHz, CDCl3): δ 3.13 (s, 3H), 3.90 (s, 3H), 4.42 (dd, 1H), 4.64 (dd, 1H), 4.86 (dd, 1H), 5.11 (dd, 1H), 5.40 (m, 1H), 7.02 (d, 2H), 8.09 (d, 2H), MS (APCI+) m/z 354 [M+H]+.

来源