Ethyl Thioglycolate → 5-(Carbethoxymethylthio)-1-(2-furyl)-1-pentanol

HRID 1389630Notes

Reaction equation

HRID 1389630 reaction equation
[SH:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].Cl[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)[OH:14].[O-]CC.[Na+]>C(O)C>[C:3]([CH2:2][S:1][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:15]1[O:16][CH:17]=[CH:18][CH:19]=1)[OH:14])([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 2723922Sodium ethoxide2×HCID 202925795-Chloro-1-(2-furyl)-1-pentanol

Product 1

HCID 202925745-(Carbethoxymethylthio)-1-(2-furyl)-1-pentanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred, refluxing mixture of 76 g of ethyl mercaptoacetate, 79.5 g of 5-chloro-1-(2-furyl)-1-pentanol (Example), and 10 ml of 1.5 M sodium ethoxide in ethanol is added an additionan 300 ml of 1.5 M sodium ethoxide during 15 minutes. 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 concentrated to give an oil, pmr spectrum (CDCl3): δ3.24 (singlet, --S--CH2CO2C2H5) and 4.70 (triplet, CH2CHOH).

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. concentrationagain concentrated
  12. customto give an oil, pmr spectrum (CDCl3)

Sources & evidence

ORD record
ord-e291fa8fd5f74f74babd6105a3df202a
Source dataset
uspto-grants-1981_01
Patent number
US04245121

Reaction notes

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