反应 #947885

反应方程式

methyl t-butyl ether

DCC

cholesterol

5-hexenoic acid

→

3-hexenoyl cholesterol

收率 95.0%

溶剂

methylene chloride

反应条件

后处理

1. 1
   其他The resulting reaction mixture
2. 2
   过滤The urea was filtered off
3. 3
   其他the product was transferred to a separatory funnel
4. 4
   洗涤washed with 1N HCl (10 mL), water (30 mL) and brine (30 mL)
5. 5
   过滤The product was filtered
6. 6
   干燥after drying over MgSO4
7. 7
   其他the solvent was evaporated
8. 8
   其他to leave a residue
9. 9
   其他The product obtained in >95% yield

实验过程

To a solution of cholesterol (2.0 g, 5.17 mM) in methylene chloride (20 mL) was added 5-hexenoic acid (0.68 mL, 5.69 mM) followed by the addition of DCC (1.60 g, 7.76 mM) and 4-PP (0.115 g, 0.78 mM) under nitrogen atmosphere. The resulting reaction mixture was stirred at ambient temperature for 1 h and worked up with the addition of methyl t-butyl ether (60 mL). The urea was filtered off, and the product was transferred to a separatory funnel, washed with 1N HCl (10 mL), water (30 mL) and brine (30 mL). The product was filtered after drying over MgSO4 and the solvent was evaporated to leave a residue. The product obtained in >95% yield was characterized by 1H NMR.

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