تفاعل #1726689

معادلة التفاعل

3-hydroxyazetidine hydrochloride

triethylamine

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

sodium cyanide

→

4A

المردود 77.0%

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

المردود 77.0%

المذيبات

methanol

methanol

dichloromethane

Water

ظروف التفاعل

المعالجة

1. 1
   أخرىSome of the desired product precipitated
2. 2
   ترشيحwas filtered off
3. 3
   ترشيحThe two layers after filtration
4. 4
   أخرىwere separated
5. 5
   استخلاصthe aqueous phase was extracted twice with dichloromethane (30 mL)
6. 6
   تجفيفThe combined organic layers were dried over MgSO4
7. 7
   أخرىthe solution was evaporated

الإجراء التجريبي

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]+.

المصدر