反応 #1726690

反応方程式

4A

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

Triethylamine

methanesulfonyl chloride

→

4B

収率 177.9%

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

収率 177.9%

溶媒

dichloromethane

反応条件

後処理

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

実験手順

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]+.

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