Reaktion #74785

Reaktionsgleichung

Water

Sodium hydride

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

m-Cyanobenzylbromide

→

oil

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

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto react to room temperature overnight
2. 2
   Extraktionthe aqueous mixture extracted with ethyl acetate (3×150 ml)
3. 3
   TrocknenThe extracts were dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated under reduced pressure

Vorschrift

Sodium hydride (50% mineral oil dispersion; 1.056 g, 0.022 mole) was added to a solution of 1,2-di-O-n-hexadecyl glycerol in tetrahydrofuran (150 ml) and stirred for 20 minutes under nitrogen. m-Cyanobenzylbromide (4.0 g, 0.020 mole) was added to the mixture and allowed to react to room temperature overnight. Water (200 ml) and then cautiously added and the aqueous mixture extracted with ethyl acetate (3×150 ml). The extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give an oil (12 g), which was chromatographed on silica gel (eluted with benzene/hexane, 8/2) resulting in pure 1,2-Di-O-(n-hexadecyl)-3-O-(3-cyanobenzyl)-glycerol (8.0 g): oil; ir(CHCl3) 2230 cm-1.

Quelle