Reacción #74785

Ecuación de reacción

Water

Sodium hydride

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

m-Cyanobenzylbromide

→

oil

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

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto react to room temperature overnight
2. 2
   Extracciónthe aqueous mixture extracted with ethyl acetate (3×150 ml)
3. 3
   SecadoThe extracts were dried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated under reduced pressure

Procedimiento

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.

Fuente