Reaction #5364

Reaction equation

KOH

methyl oleate

diiodomethane

HCl

→

cis-8-(2 -octylcyclopropyl) octanoic acid

Solvents

tetrahydrofuran methanol water

ether

Conditions

Workup

1. 1
   TemperatureThe reaction mixture is refluxed overnight
2. 2
   Extractionextracted three times with ether
3. 3
   Washwashed with brine
4. 4
   Dryingdried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   Otherto give an oil
8. 8
   Otherto give an oil free of starting material
9. 9
   Otherthe solvents are evaporated
10. 10
    Extractionextracted three times with ether
11. 11
    Extractionextracted three times with ether
12. 12
    Washwashed with brine
13. 13
    Dryingdried over, MgSO4
14. 14
    Filtrationfiltered
15. 15
    Concentrationconcentrated in vacuo

Procedure

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).

Source