海萝胶 → cis-8-(2-Octylcyclopropyl) octanoic acid

HRID 5268

反应方程式

HRID 5268 反应方程式
[C:1]([O:20]C)(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].I[CH2:23]I.Cl.[OH-].[K+]>CCOCC.[Cu].[Zn].O1CCCC1.CO.O>[CH2:11]([C@H:10]1[CH2:23][C@H:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([OH:20])=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

参与物

8

反应物 4

HCID 313海萝胶HCID 6346二碘甲烷HCID 14797氢氧化钾HCID 5364509油酸甲酯

产物 1

HCID 11426463cis-8-(2-Octylcyclopropyl) octanoic acid

试剂、催化剂与溶剂 3

HCID 10290809锌铜试剂催化剂HCID 3283乙醚溶剂HCID 21892291Methanol tetrahydrofuran water溶剂

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).

后处理

  1. temperatureThe reaction mixture is refluxed overnight
  2. extractionextracted three times with ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give an oil
  8. customto give an oil free of starting material
  9. customthe solvents are evaporated
  10. extractionextracted three times with ether
  11. extractionextracted three times with ether
  12. washwashed with brine
  13. dry with materialdried over, MgSO4
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-167d0a27c3f44fe8a981a20de9d90482
来源数据集
uspto-grants-1993_09
专利号
US05242945

关联笔记

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