Hydrochloric Acid → cis-8-(2-Octylcyclopropyl) octanoic acid

HRID 5268

反応式

HRID 5268 の反応式
[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]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 6346DiiodomethaneHCID 14797Potassium HydroxideHCID 5364509Methyl Oleate

生成物 1

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

試薬・触媒・溶媒 3

HCID 10290809Zinc copper couple触媒HCID 3283Diethyl Ether溶媒HCID 21892291Methanol tetrahydrofuran water溶媒

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).

後処理

  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

出典と根拠

ORDレコード
ord-167d0a27c3f44fe8a981a20de9d90482
出典データセット
uspto-grants-1993_09
特許番号
US05242945

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