Reaktion #1462312

Reaktionsgleichung

10-bromo-1-decanol

n-butyl lithium

1,1-(ethylenedioxy)-2-methyl-3-(phenylsulfonyl)-cyclohexane

triphenylmethane

ammonium chloride

→

1,2-(ethylenedioxy)-3-(10-hydroxydecyl)-2-methyl-3-(phenylsulfonyl)-cyclohexane

Ausbeute 92.0%

Lösungsmittel

HMPA

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe reaction was effected at room temperature for 1 hour
2. 2
   Sonstigewas then recooled to −78° C.
3. 3
   SonstigeAfter reaction at −20° C. for 2 hours
4. 4
   ExtraktionThe resulting mixture was extracted with ethyl ether
5. 5
   WaschenThe organic layer was washed with water and saturated saline
6. 6
   Trocknendried over magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent was then distilled off under reduced pressure
8. 8
   SonstigeThe residue was purified by chromatography on a silica gel column

Vorschrift

A solution of n-butyl lithium (1.02 ml) was added dropwise to a solution of 304 mg of 1,1-(ethylenedioxy)-2-methyl-3-(phenylsulfonyl)-cyclohexane and 4 mg of triphenylmethane in 5 ml of THF at −78° C. under an argon stream. After stirring for 10 minutes, the reaction was effected at room temperature for 1 hour. HMPA (1 ml) was added to the reaction mixture. It was then recooled to −78° C., followed by the dropwise addition of a solution of 90 mg of 10-bromo-1-decanol in 2 ml of THF. After reaction at −20° C. for 2 hours, the reaction mixture was poured into a saturated solution of ammonium chloride. The resulting mixture was extracted with ethyl ether. The organic layer was washed with water and saturated saline and dried over magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column while using hexane-ethyl acetate, whereby 1,2-(ethylenedioxy)-3-(10-hydroxydecyl)-2-methyl-3-(phenylsulfonyl)-cyclohexane was obtained in the form of a colorless oil. Yield: 92%, TLC: (hexane-AcOEt: 6-4) Rf=0.2

Quelle