Reaktion #351015

Reaktionsgleichung

Sodium hydride

1-trityl glycerol

1-bromohexadecane

→

1,2-dihexadecyl-3-trityl glycerol

Ausbeute 68.3%

Lösungsmittel

dimethyl formamide

dimethyl formamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   SonstigeThe reaction mixture was carefully partitioned between dichloromethane (100 ml) and water (100 ml×3)
3. 3
   WaschenThe organic layer was washed successively with saturated NaHCO3 (100 ml) and brine (100 ml)
4. 4
   Trocknendried over sodium sulphate
5. 5
   Sonstigeevaporated
6. 6
   Sonstigeto yield the crude product, which
7. 7
   Sonstigewas purified by column chromatography
8. 8
   Wascheneluting with (40-60) light petroleum: ethyl acetate (230:20)
9. 9
   workup.ADDITIONFractions containing product
10. 10
    Sonstigewere evaporated to dryness

Vorschrift

1H-nmr (200 MHz, CDCl3), 3.21 (2H, m), 3.65 (2H, m), 3.85 (1H, m), 7.4 (15H, m). ##STR17## Sodium hydride (prewashed with hexane, 60% oil dispersion, 0.79 g, 32.89 mmol) was stirred in dry dimethyl formamide (50 ml) under a stream of nitrogen. 1-trityl glycerol (5.0 g, 14.95 mmol) in dry dimethyl formamide (50 ml) was added carefully. The reaction was stirred at room temperature for 30 minutes before 1-bromohexadecane (9.13 g, 29.90 mmol) was added and the reaction was stirred at room temperature under a nitrogen atmosphere for 12 hours. The reaction mixture was carefully partitioned between dichloromethane (100 ml) and water (100 ml×3). The organic layer was washed successively with saturated NaHCO3 (100 ml) and brine (100 ml), dried over sodium sulphate and evaporated to yield the crude product, which was purified by column chromatography eluting with (40-60) light petroleum: ethyl acetate (230:20). Fractions containing product were evaporated to dryness to give 1,2-dihexadecyl-3-trityl glycerol (8.00 g, 10.21 mmol) 68% yield

Quelle