Реакция #1726691

Уравнение реакции

Ethyl acetate

(4-Mercaptophenyl)methanol

1C

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

Cs2CO3

→

5A

Выход 61.5%

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

Выход 61.5%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Температураcooled room temperature
2. 2
   Промывкаthe mixture was washed with water (50 mL)
3. 3
   ЭкстракцияThe aqueous layer was extracted with ethyl acetate (100 mL)
4. 4
   Сушкаdried (MgSO4)
5. 5
   Другоеevaporated to dryness
6. 6
   ДругоеThe residue was purified by column chromatography
7. 7
   Промывкаeluting with ethyl acetate/heptane (20:80, 40:60

Методика

(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]−.

Источник