Reaktion #526932

Reaktionsgleichung

p-toluenesulfonic acid

3-methyl pentanol

sodium hydride

dimethylformamide

bromo-alcohol

→

8-(3-methylpentyloxy)octanol

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe reaction mixture is stirred at room temperature for 17 hours
2. 2
   SonstigeThe reaction mixture is then partitioned between ethyl acetate and water
3. 3
   WaschenThe organic layer is washed with brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under vacuum
7. 7
   Sonstigeto give a yellow liquid
8. 8
   workup.STIRRINGthe reaction is stirred at room temperature for 16 hours
9. 9
   SonstigeThe methanol is removed under reduced pressure
10. 10
    Sonstigethe residue is partitioned between ethyl acetate and water
11. 11
    WaschenThe organic layer is washed with aqueous NaHCO3 and brine
12. 12
    Trocknendried over Na2SO4
13. 13
    Filtrationfiltered
14. 14
    Einengenconcentrated under vacuum

Vorschrift

To a solution of 1.67 gms of 3-methyl pentanol in 40 ml of dimethylformamide, 0.62 gms of sodium hydride are added; and the reaction mixture is stirred at room temperature for 1 hour. To this solution is added 4.0 gms of the protected bromo-alcohol and the reaction mixture is stirred at room temperature for 17 hours. The reaction mixture is then partitioned between ethyl acetate and water. The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated under vacuum to give a yellow liquid. To a solution of 4.0 gms of this liquid in 240 ml of methanol is added 0.40 gms of p-toluenesulfonic acid and the reaction is stirred at room temperature for 16 hours. The methanol is removed under reduced pressure, and the residue is partitioned between ethyl acetate and water. The organic layer is washed with aqueous NaHCO3 and brine, then dried over Na2SO4, filtered, and concentrated under vacuum to give 8-(3-methylpentyloxy)octanol.

Quelle