Ethyl Thioglycolate → HCID 20297383, compound

HRID 66413Notes

Reaction equation

HRID 66413 reaction equation
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl[CH2:9][CH2:10][CH2:11][CH:12]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)[OH:13].[O-]CC.[Na+]>C(O)C>[C:3]([CH2:2][S:1][CH2:9][CH2:10][CH2:11][CH:12]([C:14]1[O:15][CH:16]=[CH:17][CH:18]=1)[OH:13])([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxideHCID 202973764-Chloro-1-(2-furyl)-1-butanol

Product 1

HCID 20297383HCID 20297383, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred, refluxing mixture of ethyl mercaptoacetate, and 4-chloro-1-(2-furyl)-1-butanol (Example 160), and sodium ethoxide in ethanol. The resulting mixture is stirred at reflux for 3 hours, cooled, and concentrated to remove most of the ethanol. The residue is partitioned with ether and water. The ether phase is washed with brine and dried over potassium carbonate. The solution is concentrated, diluted with xylene, and again conentrated to give an oil.

Workup

  1. temperatureTo a stirred, refluxing
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customto remove most of the ethanol
  6. customThe residue is partitioned with ether and water
  7. washThe ether phase is washed with brine
  8. dry with materialdried over potassium carbonate
  9. concentrationThe solution is concentrated
  10. additiondiluted with xylene
  11. customto give an oil

Sources & evidence

ORD record
ord-6777cfb605da49a5bf335c261b83cb5c
Source dataset
uspto-grants-1978_12
Patent number
US04131737

Reaction notes

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