반응 #5364

반응 방정식

KOH

methyl oleate

diiodomethane

HCl

→

cis-8-(2 -octylcyclopropyl) octanoic acid

용매

tetrahydrofuran methanol water

ether

반응 조건

후처리

1. 1
   온도The reaction mixture is refluxed overnight
2. 2
   추출extracted three times with ether
3. 3
   세척washed with brine
4. 4
   건조dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타to give an oil
8. 8
   기타to give an oil free of starting material
9. 9
   기타the solvents are evaporated
10. 10
    추출extracted three times with ether
11. 11
    추출extracted three times with ether
12. 12
    세척washed with brine
13. 13
    건조dried over, MgSO4
14. 14
    여과filtered
15. 15
    농축concentrated in vacuo

실험 절차

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).

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