反応 #1122410

反応方程式

Ethyl acetate

(4-Mercaptophenyl)methanol

53B

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

Cs2CO3

→

60A

収率 61.5%

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

収率 61.5%

溶媒

DMF

反応条件

後処理

1. 1
   温度cooled room temperature
2. 2
   洗浄the mixture was washed with water (50 mL)
3. 3
   抽出The aqueous layer was extracted with ethyl acetate (100 mL)
4. 4
   乾燥dried (MgSO4)
5. 5
   その他evaporated to dryness
6. 6
   その他The residue was purified by column chromatography
7. 7
   洗浄eluting with ethyl acetate/heptane (20:80, 40:60

実験手順

(4-Mercaptophenyl)methanol (2.38 g, 17.0 mmol) and 53B (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 60A 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]+.

出典