Reaktion #343596

Reaktionsgleichung

diisopropylamine

n-butyllithium

2-benzyloxybenzyl chloride

methyl cyclohexancarboxylate

→

viscous oil

Ausbeute 70.0%

Methyl 1-(2-benzyloxyphenyl)methylcyclohexan-1-carboxylate

Ausbeute 70.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto warm to 0° C.
2. 2
   workup.STIRRINGStirring
3. 3
   workup.WAITwas continued for 45 minutes
4. 4
   workup.STIRRINGThe resulting mixture was stirred at room temperature for 24 hours
5. 5
   Sonstigequenched by addition of 150 ml 3M acetic acid
6. 6
   workup.STIRRINGstirred at room temperature for one week
7. 7
   workup.ADDITIONThe mixture was diluted with ethyl ether
8. 8
   Waschenwashed with sodium bicarbonate solution, brine
9. 9
   Trocknendried (MgSO4)
10. 10
    Einengenconcentrated to a yellow oil, 29.3 g
11. 11
    workup.DISTILLATIONThis was distilled

Vorschrift

Under anhydrous conditions and a nitrogen atmoshere a solution of 8.7 g (0.086 mole) diisopropylamine in 250 ml tetrahydrofuran was cooled to -78° C. and 1.6M n-butyllithium (53.75 ml, 0.086 mole) was added dropwise over ten minutes. The mixture was stirred for 45 minutes, allowed to warm to 0° C. and 12.2 g (0.086 mole) methyl cyclohexancarboxylate was added. Stirring was continued for 45 minutes and then 20 g (0.086 mole) 2-benzyloxybenzyl chloride in 20 ml tetrahydrofuran was added dropwise. The resulting mixture was stirred at room temperature for 24 hours, quenched by addition of 150 ml 3M acetic acid and stirred at room temperature for one week. The mixture was diluted with ethyl ether, washed with sodium bicarbonate solution, brine, dried (MgSO4) and concentrated to a yellow oil, 29.3 g. This was distilled to obtain 20.23 g (70%) of viscous oil, b.p. 135°-140° C. (0.4 Torr).

Quelle