Réaction #217075

Équation de réaction

Sodium hydride

1-bromo-10-undecene

N-methylacetamide

1-Octylamino-10-hydroxy-11-(N-methylacetamido)undecane

→

1-(N-methylacetamido)-10-undecene

Rendement 57.0%

Solvants

water

DMSO

Conditions de réaction

Traitement

1. 1
   Extractionextracted with dichloromethane (3×100 mL)
2. 2
   LavageThe combined extracts were washed with water (70 mL) and saturated aqueous salt solution (70 mL)
3. 3
   Séchagedried over sodium sulfate
4. 4
   AutreThe solvent was evaporated under vacuum
5. 5
   Autreto give a yellow residue, which
6. 6
   Autrewas chromatographed (silica/ethyl acetate)

Mode opératoire

This example illustrates a synthesis of 1-Octylamino-10-hydroxy-11-(N-methylacetamido)undecane (compound no. 77). Sodium hydride (0.56 g, 23 mmol) was added to a solution of 1-bromo-10-undecene (5.4 g, 23 mmol) and N-methylacetamide (91.7 g, 23 mmol) in DMSO (40 mL). After 8 hours, the reaction was complete and the mixture added to water (100 mL) and extracted with dichloromethane (3×100 mL). The combined extracts were washed with water (70 mL) and saturated aqueous salt solution (70 mL), and dried over sodium sulfate. The solvent was evaporated under vacuum to give a yellow residue, which was chromatographed (silica/ethyl acetate), yielding 2.95 g of 1-(N-methylacetamido)-10-undecene as a colorless oil (57% yield).

Source