Triethylamine → Methyl toluenesulfonyloxyacetate

HRID 1940259

Reaktionsgleichung

Reaktionsgleichung von HRID 1940259
[OH:1][CH2:2][C:3]([O:5][CH3:6])=[O:4].C(N(CC)CC)C.[C:14]1([CH3:24])[C:15]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1>ClCCl>[C:14]1([CH3:24])[C:15]([S:20]([O:1][CH2:2][C:3]([O:5][CH3:6])=[O:4])(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 8623o-Toluenesulfonyl chlorideHCID 66774Methyl Glycolate

Produkt 1

HCID 86751745Methyl toluenesulfonyloxyacetateAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

18 g (0.2 mol) of methyl hydroxyacetate and 20.2 g (0.2 mol) of triethylamine are first introduced into 300 ml of dichloromethane at 0° C. 41.9 g (0.22 mol) of toluenesulfonyl chloride are then added at this temperature in small portions. Stirring of the batch at 0° C. is continued overnight. Ice water is added, the phases are separated, and the aqueous phase is extracted three times with dichloromethane. The combined organic phases are washed once with water, dried, and the solvent is removed on a rotary evaporator. 48 g (98% of theory) of methyl toluenesulfonyloxyacetate having a GC content of 96% are isolated as a colorless solid.

Aufarbeitung

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted three times with dichloromethane
  3. washThe combined organic phases are washed once with water
  4. customdried
  5. customthe solvent is removed on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-49cbc3da55944ccc97d427074c032aa5
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05698735

Verknüpfte Notizen

Wird geladen…