Reaktion #1726691

Reaktionsgleichung

Ethyl acetate

(4-Mercaptophenyl)methanol

1C

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

Cs2CO3

→

5A

Ausbeute 61.5%

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

Ausbeute 61.5%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled room temperature
2. 2
   Waschenthe mixture was washed with water (50 mL)
3. 3
   ExtraktionThe aqueous layer was extracted with ethyl acetate (100 mL)
4. 4
   Trocknendried (MgSO4)
5. 5
   Sonstigeevaporated to dryness
6. 6
   SonstigeThe residue was purified by column chromatography
7. 7
   Wascheneluting with ethyl acetate/heptane (20:80, 40:60

Vorschrift

(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]−.

Quelle