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

HRID 1389330

Reaktionsgleichung

Reaktionsgleichung von HRID 1389330
[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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred, refluxing mixture of 76 g of ethyl mercaptoacetate, 79.5 g of 5-chloro-1-(2-furyl)-1-pentanol (Example 55), and 10 ml of 1.5 M sodium ethoxide in ethanol is added an additional 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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-8aa1321754ac49dcb35ed01487bba8f2
Quelldatensatz
uspto-grants-1981_01
Patentnummer
US04243817

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