تفاعل #1726696

معادلة التفاعل

4-Hydroxybenzaldehyde

cesium carbonate

4B

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

→

9A

المردود 62.1%

4-(1-(5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde

المردود 62.1%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthen cooled to RT
2. 2
   ترشيحThe solids were filtered off
3. 3
   أخرىthe filtrate was evaporated
4. 4
   workup.ADDITIONThe residue was treated with methanol
5. 5
   أخرىthe solid formed
6. 6
   ترشيحwas collected by filtration
7. 7
   أخرىDrying under vacuum

الإجراء التجريبي

4-Hydroxybenzaldehyde (1.10 g, 9.17 mmol), cesium carbonate (3.49 g, 10.70 mmol) and 4B (2.70 g, 7.64 mmol) were mixed with DMF (80 mL). The mixture was stirred at 110° C. for 18 h then cooled to RT. The solids were filtered off and the filtrate was evaporated. The residue was treated with methanol and the solid formed was collected by filtration. Drying under vacuum gave 1.8 g (62%) of 9A as a beige solid. 1H NMR (500 MHz, DMSO-d6): δ 3.85 (s, 3H), 4.13 (dd, 1H), 4.57 (dd, 1H), 4.65 (dd, 1H), 5.12 (dd, 1H), 5.29 (m, 1H), 7.10 (d, 2H), 7.16 (d, 2H), 7.90 (d, 2H), 8.00 (d, 2H), 9.90 (s, 1H), MS (APCI+) m/z 380 [M+H]+.

المصدر