Reaction #1726691

Reaction equation

Ethyl acetate

(4-Mercaptophenyl)methanol

1C

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

Cs2CO3

→

5A

Yield 61.5%

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

Yield 61.5%

Solvents

DMF

Conditions

Workup

1. 1
   Temperaturecooled room temperature
2. 2
   Washthe mixture was washed with water (50 mL)
3. 3
   ExtractionThe aqueous layer was extracted with ethyl acetate (100 mL)
4. 4
   Dryingdried (MgSO4)
5. 5
   Otherevaporated to dryness
6. 6
   OtherThe residue was purified by column chromatography
7. 7
   Washeluting with ethyl acetate/heptane (20:80, 40:60

Procedure

(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