p-Toluenesulfonic acid monohydrate → tetrahydro-3-hydroxy-(R)-6-undecyl-2H-pyran-2-one

HRID 6057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 6057
C([C@H](C(O)CC([O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1)CCCCCCCCCCC)C(O)=O)CCCCC.[OH2:33].[C:34]1([CH3:44])[CH:39]=[CH:38][C:37](S(O)(=O)=O)=[CH:36][CH:35]=1>C(O)C>[OH:33][C@@H:31]1[CH2:30][CH2:29][CH:28]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:34][CH3:44])[O:27][C:26]1=[O:25]

Komponenten

4

Edukt 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 678557542-hexyl-3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoic acid

Produkt 1

HCID 67855761tetrahydro-3-hydroxy-(R)-6-undecyl-2H-pyran-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

M)a) 15.4 g of a diastereomer mixture of 2-hexyl-3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoic acid were dissolved in 160 ml of ethanol and 800 mg of toluene-4-sulfonic acid monohydrate were added. The reaction mixture was heated to 55°-60° C. until the reaction was finished. The solvent was removed in vacuo and the residue was dissolved in 160 ml of dichloromethane. The solution was stirred at room temperature for 1 hour. The reaction mixture was evaporated. The material obtained was chromatographed on silica gel. There was obtained tetrahydro-3-hydroxy-(R)-6-undecyl-2H-pyran-2-one, m.p. 95°-96° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated to 55°-60° C. until the reaction
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 160 ml of dichloromethane
  4. customThe reaction mixture was evaporated
  5. customThe material obtained
  6. customwas chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-79667b592cd94ca2943c996933ceac25
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246960

Notizen zur Reaktion

Wird geladen…