Реакция #1726696

Уравнение реакции

4-Hydroxybenzaldehyde

cesium carbonate

4B

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

→

9A

Выход 62.1%

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

Выход 62.1%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Температураthen cooled to RT
2. 2
   ФильтрацияThe solids were filtered off
3. 3
   Другоеthe filtrate was evaporated
4. 4
   workup.ADDITIONThe residue was treated with methanol
5. 5
   Другоеthe solid formed
6. 6
   Фильтрацияwas collected by filtration
7. 7
   ДругоеDrying under vacuum

Методика

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]+.

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