Reaction #1726696

Reaction equation

4-Hydroxybenzaldehyde

cesium carbonate

4B

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

→

9A

Yield 62.1%

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

Yield 62.1%

Solvents

DMF

Conditions

Workup

1. 1
   Temperaturethen cooled to RT
2. 2
   FiltrationThe solids were filtered off
3. 3
   Otherthe filtrate was evaporated
4. 4
   workup.ADDITIONThe residue was treated with methanol
5. 5
   Otherthe solid formed
6. 6
   Filtrationwas collected by filtration
7. 7
   OtherDrying under vacuum

Procedure

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]+.

Source