Réaction #2195476

Équation de réaction

triethylamine

Linoleyl alcohol

Methanesulfonyl chloride

→

colorless oil

Rendement 97.0%

Linoleyl Mesylate

Rendement 97.0%

Solvants

DCM

DCM

Conditions de réaction

Traitement

1. 1
   AutreThe flask was sealed
2. 2
   Autreflushed with argon
3. 3
   workup.ADDITIONadded slowly to the stirring reaction mixture
4. 4
   Lavagewashed with saturated bicarbonate solution (2×200 mL)
5. 5
   SéchageThe organic phase was dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated

Mode opératoire

Linoleyl alcohol (10.0 g, 37.5 mmol) was weighed into a 500 mL round bottomed flask with a stir bar. The flask was sealed, flushed with argon, charged with DCM (100 mL) and triethylamine (7.84 mL, 1.5 equiv.) and cooled to 0° C. Methanesulfonyl chloride (4.35 mL), 1.5 equiv.) was measured in a PP syringe and added slowly to the stirring reaction mixture. TLC analysis (7.5% EtOAc/Hexanes) showed the reaction was complete within 1 hr. The reaction was diluted with DCM (100 mL) and washed with saturated bicarbonate solution (2×200 mL). The organic phase was dried over MgSO4, filtered and concentrated to give 12.53 g (97%) of colorless oil that was used without further purification.

Source