Réaction #1726690

Équation de réaction

4A

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

Triethylamine

methanesulfonyl chloride

→

4B

Rendement 177.9%

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

Rendement 177.9%

Solvants

dichloromethane

Conditions de réaction

Traitement

1. 1
   Températurewas cooled in an ice-bath
2. 2
   workup.ADDITIONAfter the addition
3. 3
   Autrethe cooling bath was removed
4. 4
   AutreThe mixture was transferred to a separatory funnel
5. 5
   Lavagewas washed with water
6. 6
   AutreThe organic solution was dried (phase separator)
7. 7
   Autreevaporated
8. 8
   workup.ADDITIONDichloromethane (50 mL) and diethyl ether (200 mL) were added
9. 9
   Filtrationthe solid product was filtered
10. 10
    LavageThe product was washed twice with diethyl ether
11. 11
    Autredried in vacuo

Mode opératoire

A suspension of 4A (5.45 g, 19. 8 mmol) in dichloromethane (100 mL) was cooled in an ice-bath. Triethylamine (4.4 mL, 31.7 mmol) was added followed by methanesulfonyl chloride (2.3 mL, 29.7 mmol). After the addition, the cooling bath was removed. The mixture was stirred for 7 h. The mixture was transferred to a separatory funnel and was washed with water followed by aqueous NaHCO3 (sat.). The organic solution was dried (phase separator) and evaporated. Dichloromethane (50 mL) and diethyl ether (200 mL) were added and the solid product was filtered. The product was washed twice with diethyl ether and then dried in vacuo. There was obtained 5.03 g (72%) of 4B as a solid. 1H NMR (500 MHz, CDCl3): δ 3.13 (s, 3H), 3.90 (s, 3H), 4.42 (dd, 1H), 4.64 (dd, 1H), 4.86 (dd, 1H), 5.11 (dd, 1H), 5.40 (m, 1H), 7.02 (d, 2H), 8.09 (d, 2H), MS (APCI+) m/z 354 [M+H]+.

Source