Реакция #5364

Уравнение реакции

KOH

methyl oleate

diiodomethane

HCl

→

cis-8-(2 -octylcyclopropyl) octanoic acid

Растворители

tetrahydrofuran methanol water

ether

Условия реакции

Обработка

1. 1
   ТемператураThe reaction mixture is refluxed overnight
2. 2
   Экстракцияextracted three times with ether
3. 3
   Промывкаwashed with brine
4. 4
   Сушкаdried over MgSO4
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated in vacuo
7. 7
   Другоеto give an oil
8. 8
   Другоеto give an oil free of starting material
9. 9
   Другоеthe solvents are evaporated
10. 10
    Экстракцияextracted three times with ether
11. 11
    Экстракцияextracted three times with ether
12. 12
    Промывкаwashed with brine
13. 13
    Сушкаdried over, MgSO4
14. 14
    Фильтрацияfiltered
15. 15
    Концентрированиеconcentrated in vacuo

Методика

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).

Источник