Reaktion #1726689

Reaktionsgleichung

3-hydroxyazetidine hydrochloride

triethylamine

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

sodium cyanide

→

4A

Ausbeute 77.0%

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

Ausbeute 77.0%

Lösungsmittel

methanol

methanol

dichloromethane

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeSome of the desired product precipitated
2. 2
   Filtrationwas filtered off
3. 3
   FiltrationThe two layers after filtration
4. 4
   Sonstigewere separated
5. 5
   Extraktionthe aqueous phase was extracted twice with dichloromethane (30 mL)
6. 6
   TrocknenThe combined organic layers were dried over MgSO4
7. 7
   Sonstigethe solution was evaporated

Vorschrift

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]+.

Quelle