Hydrochloric Acid → 2-(6-Carbethoxyhexyl)-3-heptylthio-cyclopentanone

HRID 1580336Notes

Reaction equation

HRID 1580336 reaction equation
[N+](=[CH:3][CH3:4])=[N-].[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH:18]([S:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:17][CH2:16][C:15]1=[O:27])([OH:7])=[O:6].C(O)C.Cl>CCOCC>[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]1[CH:18]([S:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:17][CH2:16][C:15]1=[O:27])([O:7][CH2:3][CH3:4])=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 70695DiazoethaneHCID 215661202-(6-Carboxyhexyl)-3-heptylthio-cyclopentanone

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

At room temperature, 70 ml. of a 0.2N diazoethane solution in ether is added to a solution of 3.4 g. of 2-(6-carboxyhexyl)-3-heptylthio-cyclopentanone in 25 ml. of dry ethanol. The reaction mixture is poured into 100 ml. of ice water, containing 5 ml. of concentrated HCl, agitated, the organic phase separated, the aqueous phase extracted three times with respectively 30 ml. of chloroform, and the combined organic phases are washed with water, dried over Na2SO4, the solvent is distilled off, and chromatographic purification of the residue (silica gel/chloroform) produces 2-(6-carbethoxyhexyl)-3-heptylthio-cyclopentanone. Rf = 0.7 (silica gel/chloroform).

Workup

  1. customAt room temperature
  2. additionThe reaction mixture is poured into 100 ml
  3. customthe organic phase separated
  4. extractionthe aqueous phase extracted three times with respectively 30 ml
  5. washof chloroform, and the combined organic phases are washed with water
  6. dry with materialdried over Na2SO4
  7. distillationthe solvent is distilled off
  8. customchromatographic purification of the residue (silica gel/chloroform)

Sources & evidence

ORD record
ord-4a44d19ff02b4e7c833af13c91918067
Source dataset
uspto-grants-1976_01
Patent number
US03932487

Reaction notes

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