Ethyl 5-oxocyclopent-1-ene-1-heptanoate → 2-(6-Carbethoxyhexyl)-3-heptylthio-cyclopentanone

HRID 1580333Notes

Reaction equation

HRID 1580333 reaction equation
[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[C:13](=[O:17])[CH2:14][CH2:15][CH:16]=1)([O:3][CH2:4][CH3:5])=[O:2].[CH2:18]([S-:25])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[Na+]>C(O)C>[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH:16]([S:25][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:15][CH2:14][C:13]1=[O:17])([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 15573491Ethyl 5-oxocyclopent-1-ene-1-heptanoateHCID 23688245Sodium heptanethiolate

Product 1

HCID 215661732-(6-Carbethoxyhexyl)-3-heptylthio-cyclopentanone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.2 g. of 2-(6-carbethoxyhexyl)-2-cyclopentenone, dissolved in 20 ml. of dry ethanol, is added to a solution of sodium heptanethiolate (producible by dissolving 0.24 g. of sodium in 30 ml. of dry ethanol and adding 1.3 g. of heptylthiol); the reaction mixture is agitated under nitrogen for 24 hours at 40°, then diluted with 150 ml. of ice water and 10 ml. of concentrated HCl, extracted with CH2Cl2, washed with saturated aqueous NaCl solution, dried over Na2SO4, and the solvent is distilled off. After purifying the residue by chromatography, 2-(6-carbethoxyhexyl)-3-heptylthio-cyclopentanone is obtained. Rf = 0.7 (silica gel/chloroform).

Workup

  1. additiondiluted with 150 ml
  2. extractionof concentrated HCl, extracted with CH2Cl2
  3. washwashed with saturated aqueous NaCl solution
  4. dry with materialdried over Na2SO4
  5. distillationthe solvent is distilled off
  6. customAfter purifying the residue by chromatography

Sources & evidence

ORD record
ord-6d5f7a6b47704b9191fb06e97e206ad2
Source dataset
uspto-grants-1976_01
Patent number
US03932487

Reaction notes

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