反応 #5364

反応方程式

KOH

methyl oleate

diiodomethane

HCl

→

cis-8-(2 -octylcyclopropyl) octanoic acid

溶媒

tetrahydrofuran methanol water

ether

反応条件

後処理

1. 1
   温度The reaction mixture is refluxed overnight
2. 2
   抽出extracted three times with ether
3. 3
   洗浄washed with brine
4. 4
   乾燥dried over MgSO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated in vacuo
7. 7
   その他to give an oil
8. 8
   その他to give an oil free of starting material
9. 9
   その他the solvents are evaporated
10. 10
    抽出extracted three times with ether
11. 11
    抽出extracted three times with ether
12. 12
    洗浄washed with brine
13. 13
    乾燥dried over, MgSO4
14. 14
    ろ過filtered
15. 15
    濃縮concentrated in vacuo

実験手順

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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