Réaction #1726691

Équation de réaction

Ethyl acetate

(4-Mercaptophenyl)methanol

1C

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

Cs2CO3

→

5A

Rendement 61.5%

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

Rendement 61.5%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Températurecooled room temperature
2. 2
   Lavagethe mixture was washed with water (50 mL)
3. 3
   ExtractionThe aqueous layer was extracted with ethyl acetate (100 mL)
4. 4
   Séchagedried (MgSO4)
5. 5
   Autreevaporated to dryness
6. 6
   AutreThe residue was purified by column chromatography
7. 7
   Lavageeluting with ethyl acetate/heptane (20:80, 40:60

Mode opératoire

(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]−.

Source