反応 #1726689

反応方程式

3-hydroxyazetidine hydrochloride

triethylamine

ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate

sodium cyanide

→

4A

収率 77.0%

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

収率 77.0%

溶媒

methanol

methanol

dichloromethane

Water

反応条件

後処理

1. 1
   その他Some of the desired product precipitated
2. 2
   ろ過was filtered off
3. 3
   ろ過The two layers after filtration
4. 4
   その他were separated
5. 5
   抽出the aqueous phase was extracted twice with dichloromethane (30 mL)
6. 6
   乾燥The combined organic layers were dried over MgSO4
7. 7
   その他the solution was evaporated

実験手順

To a suspension of ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate—see e.g. Journal fuer Praktische Chemie, 327, 109-116 (1985)—(0.50 g, 2.01 mmol) in dry methanol (10 mL) was added sodium cyanide (20 mg, 0.40 mmol). A solution of 3-hydroxyazetidine hydrochloride (0.26 g, 2.42 mmol) in methanol (2 mL) and then triethylamine (0.34 mL, 2.42 mmol) were added at ambient temperature. The reaction mixture was stirred at ambient temperature overnight. Water (20 mL) and dichloromethane (30 mL) were added. Some of the desired product precipitated and was filtered off. The two layers after filtration were separated and the aqueous phase was extracted twice with dichloromethane (30 mL). The combined organic layers were dried over MgSO4 and the solution was evaporated. In total, there was obtained 0.43 g (77%) of 4A as a solid. 1H NMR (400 MHz, DMSO-d6): δ 3.82 (dd, 1H), 3.84 (s, 3H), 4.30 (m, 2H), 4.55 (m, 1H), 4.77 (dd, 1H), 5.85 (d, 1H), 7.16 (d, 2H), 7.98 (d, 2H), MS (APCI+) m/z 276 [M+H]+.

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