Reacción #1726691

Ecuación de reacción

Ethyl acetate

(4-Mercaptophenyl)methanol

1C

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

Cs2CO3

→

5A

Rendimiento 61.5%

(3-(4-(Hydroxymethyl)phenylthio)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone

Rendimiento 61.5%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled room temperature
2. 2
   Lavadothe mixture was washed with water (50 mL)
3. 3
   ExtracciónThe aqueous layer was extracted with ethyl acetate (100 mL)
4. 4
   Secadodried (MgSO4)
5. 5
   Otroevaporated to dryness
6. 6
   OtroThe residue was purified by column chromatography
7. 7
   Lavadoeluting with ethyl acetate/heptane (20:80, 40:60

Procedimiento

(4-Mercaptophenyl)methanol (2.38 g, 17.0 mmol) and 1C (5.00 g, 15.5 mmol) were mixed in DMF (80 mL). Cs2CO3 (6.05 g, 18.56 mmol) was added. The mixture was stirred at 90° C. overnight and then cooled room temperature. Ethyl acetate (150 mL) was added and the mixture was washed with water (50 mL). The aqueous layer was extracted with ethyl acetate (100 mL). The organic phases were combined, dried (MgSO4) and evaporated to dryness. The residue was purified by column chromatography eluting with ethyl acetate/heptane (20:80, 40:60 and then 60:40). There was obtained 3.5 g (61%) of 5A as a solid. 1H NMR (500 MHz, CDCl3): δ 4.19 (m, 2H), 4.64 (m, 2H), 4.69 (s, 2H), 5.10 (m, 1H), 7.34 (m, 4H), 7.53 (t, 2H), 7.59 (t, 1H), 8.15 (d, 2H), MS (APCI+) m/z 368 [M−H]−.

Fuente