反应 #2507836

反应方程式

pentane

3-methyl-2-butenoic acid

4-methoxythiophenol

piperidine

→

3-(4-methoxyphenylthio)-3-methyl-butyric acid

溶剂

ethyl acetate

反应条件

后处理

1. 1
   温度cooled to room temperature
2. 2
   洗涤the resulting solution was washed with 1M aqueous HCl (50 ml×2), water (50 ml), and saturated aqueous NaCl (50 ml)
3. 3
   干燥The organic solution was thereafter dried over NaSO4
4. 4
   其他Concentration of this organic solution under reduced pressure afforded an oil and 2 days incubation at −20° C.
5. 5
   其他yielded a crystalline solid
6. 6
   其他was then crushed
7. 7
   过滤filtered
8. 8
   洗涤The solid was washed
9. 9
   过滤on filter paper with pentane (20 ml, 2 times)

实验过程

A heavy-walled screw-cap tube was charged with 3-methyl-2-butenoic acid (13.86 gm) 3,3-dimethylacrylic acid, (138.4 mmol), 4-methoxythiophenol (143.2 mmol), and piperidine (41.6 mmol) [Aldrich]. The mixture was heated to 105-110° C. for 32 hours, then cooled to room temperature. The reaction mixture was dissolved in ethyl acetate (EtOAc) (700 ml) with stirring, and the resulting solution was washed with 1M aqueous HCl (50 ml×2), water (50 ml), and saturated aqueous NaCl (50 ml). The organic solution was thereafter dried over NaSO4. Concentration of this organic solution under reduced pressure afforded an oil and 2 days incubation at −20° C. yielded a crystalline solid. Forty ml of pentane were added to the solid, which was then crushed and filtered. The solid was washed on filter paper with pentane (20 ml, 2 times) to yield the product 3-(4-methoxyphenylthio)-3-methyl-butyric acid, as pale yellow crystals (31.4 grams, 94.4% yield, m.p. 62-64° C.), [1H-NMR(CDCl3): d7.5 (t, 2H, J=8 Hz), d6.9 (t, 2H, J=6.7 Hz), d3.9 (s, 3H, J=16.1 Hz), d2.6 (s, 2H), d1.3 (s, 6H)].

来源