Propyl mercaptan → 2-(Carbethoxyhexyl)-3-propylthio-cyclopentanone

HRID 1580334Notes

Reaction equation

HRID 1580334 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]([SH:21])[CH2:19][CH3:20].N1CCCCC1>>[C:1]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]1[CH:16]([S:21][CH2:18][CH2:19][CH3:20])[CH2:15][CH2:14][C:13]1=[O:17])([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 3

HCID 7848Propyl mercaptanHCID 8082PiperidineHCID 15573491Ethyl 5-oxocyclopent-1-ene-1-heptanoate

Product 1

HCID 543939182-(Carbethoxyhexyl)-3-propylthio-cyclopentanone

Procedure

A mixture of 6 g. of 2-(6-carbethoxyhexyl)-2-cyclopentenone, 10 ml. of propanethiol, and 7.2 ml. of piperidine is allowed to stand for 5 days at room temperature, then diluted with 150 ml. of ether, and the ether phase is washed first with a mixture of 60 ml. of ice water and 6 ml. of concentrated HCl, and then with saturated aqueous NaCl solution, dried over NaSO4, and the solvent distilled off. After purifying the residue by chromatography (silica gel/chloroform), 2-(carbethoxyhexyl)-3-propylthio-cyclopentanone is produced as an oil.

Workup

  1. additionA mixture of 6 g
  2. additiondiluted with 150 ml
  3. washof ether, and the ether phase is washed first with a mixture of 60 ml
  4. dry with materialof concentrated HCl, and then with saturated aqueous NaCl solution, dried over NaSO4
  5. distillationthe solvent distilled off
  6. customAfter purifying the residue by chromatography (silica gel/chloroform)

Sources & evidence

ORD record
ord-2afee92f26cd42c1a06153d2a22a6a4b
Source dataset
uspto-grants-1976_01
Patent number
US03932487

Reaction notes

Loading…