反应 #5364

反应方程式

KOH

methyl oleate

diiodomethane

HCl

→

cis-8-(2 -octylcyclopropyl) octanoic acid

溶剂

tetrahydrofuran methanol water

ether

反应条件

后处理

1. 1
   温度The reaction mixture is refluxed overnight
2. 2
   萃取extracted three times with ether
3. 3
   洗涤washed with brine
4. 4
   干燥dried over MgSO4
5. 5
   过滤filtered
6. 6
   浓缩concentrated in vacuo
7. 7
   其他to give an oil
8. 8
   其他to give an oil free of starting material
9. 9
   其他the solvents are evaporated
10. 10
    萃取extracted three times with ether
11. 11
    萃取extracted three times with ether
12. 12
    洗涤washed with brine
13. 13
    干燥dried over, MgSO4
14. 14
    过滤filtered
15. 15
    浓缩concentrated in vacuo

实验过程

To 2.2 g of zinc-copper couple in 30 mL of dry ether is added 5.7 mL (16.9 mmol) of methyl oleate and 5.4 mL (70.7 mmol) of diiodomethane. The reaction mixture is refluxed overnight, cooled to room temperature, poured into 1.0N HCl, and extracted three times with ether. The organic layers are combined, washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give an oil. The oil is subjected to the conditions described in Example 51 above to give an oil free of starting material. The oil is taken up in a combination of tetrahydrofuran:methanol:water (2:1:1), followed by the addition of 4.0 g of 85% KOH. After 4 hours stirring at room temperature, the solvents are evaporated, the residue taken up in 0.1N KOH, and extracted three times with ether. The aqueous phase is acidified using concentrated HCl and extracted three times with ether. The ether layers are combined, washed with brine, dried over, MgSO4, filtered, and concentrated in vacuo to give cis-8-(2 -octylcyclopropyl) octanoic acid. Spectral data follows: 1H NMR (CDCl3, 400 MHz) δ 2.35 (t, 2H, J=7.0 Hz, CH2C=O), 0.6-1.7 (m, 33H).

来源