Reaktion #531245

Reaktionsgleichung

Water

Sodium hydride

1,2-di-O-(n-hexadecyl)-glycerol

m-Cyanobenzyl bromide

→

1,2-Di-O-(n-hexadecyl)-3-O-(3-cyanobenzyl)-glycerol

Ausbeute 68.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture stirred overnight at room temperature under nitrogen
2. 2
   Extraktionthe resulting mixture extracted with ethyl acetate (3×150 ml.)
3. 3
   ExtraktionThe combined ethyl acetate extract
4. 4
   Trocknenwas dried (MgSO4)
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated in vacuo to an oil (12 g.), which
7. 7
   Sonstigewas purified by silica gel chromatography (elution with benzene:hexane) [8.0 g., 68% yield, oil, ir (CHCl3) 2230 cm-1 ]

Vorschrift

Sodium hydride (1.056 g. of 50 wt. % mineral oil dispersion, 22 mmoles) was added to a solution of 1,2-di-O-(n-hexadecyl)-glycerol (9.73 g., 18 mmoles) in tetrahydrofuran (150 ml.) and the resulting solution stirred for 20 minutes at room temperature under nitrogen. m-Cyanobenzyl bromide (4.0 g., 20 mmoles) was added and the reaction mixture stirred overnight at room temperature under nitrogen. Water (200 ml.) was then added cautiously and the resulting mixture extracted with ethyl acetate (3×150 ml.). The combined ethyl acetate extract was dried (MgSO4), filtered and evaporated in vacuo to an oil (12 g.), which was purified by silica gel chromatography (elution with benzene:hexane) [8.0 g., 68% yield, oil, ir (CHCl3) 2230 cm-1 ].

Quelle