Reaktion #1160194

Reaktionsgleichung

2

cis-9-Octadecenoic acid 2,3-dihydroxypropyl ester

triphenylmethyl chloride

→

colorless oil

Ausbeute 88.0%

cis-9-Octadecenoic acid 2-hydroxy-3-triphenylmethoxypropyl ester

Ausbeute 88.0%

Lösungsmittel

dichloromethane pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent is removed
2. 2
   workup.ADDITIONthe residue is added twice with 50 ml of toluene
3. 3
   Einengenconcentrated
4. 4
   workup.ADDITIONThe residue is diluted with 100 ml of H2O
5. 5
   Extraktionextracted three times with 50 ml of dichloromethane
6. 6
   WaschenThe combined organic phases are washed with 50 ml of cold 5% HCl and 50 ml of saturated NaCl solution
7. 7
   Trocknendried over MgSO4
8. 8
   Filtrationfiltrated
9. 9
   Einengenconcentrated
10. 10
    SonstigeThe residue is purified by chromatography on silica gel

Vorschrift

A solution of 2 (21 mmol) in 80 ml of dichloromethane/pyridine (1:1) is added dropwise with triphenylmethyl chloride (27 mmol) and stirred at room temperature for 48 hours. The solvent is removed, and the residue is added twice with 50 ml of toluene and concentrated. The residue is diluted with 100 ml of H2O and extracted three times with 50 ml of dichloromethane. The combined organic phases are washed with 50 ml of cold 5% HCl and 50 ml of saturated NaCl solution, dried over MgSO4, filtrated and concentrated. The residue is purified by chromatography on silica gel using heptane/ethyl acetate (5:1). Yield: 88% of a colorless oil.

Quelle