Реакция #2146730

Уравнение реакции

cyclohexanone

HCl

tert-butyllithium

pentane

isobutyl iodide

→

1-isobutylcyclohexanol

Растворители

diethyl ether

Условия реакции

Обработка

1. 1
   Температураwarmed to 10° C.
2. 2
   Температураcooled to −70° C.
3. 3
   workup.ADDITIONAt the end of the addition
4. 4
   Другоеto reach room temperature
5. 5
   ЭкстракцияThe water phase was extracted with diethyl ether (300 ml)
6. 6
   Промывкаthe combined organic phases were washed with water (400 ml) and aqueous saturated NaCl solution (500 ml)
7. 7
   Сушкаdried (50 g MgSO4)
8. 8
   Другоеthe solvent evaporated

Методика

At −60° C., a solution of 1.7M tert-butyllithium in pentane (1000 ml, 1.7 mol, 2.1 eq.) in diethyl ether (800 ml) was treated dropwise within 1 h with isobutyl iodide (157 g, 0.81 mol, 1.0 eq.). The resulting solution was stirred at −70° C. for 45 min., warmed to 10° C., cooled to −70° C., and treated at this temperature within 4 h with cyclohexanone (100.7 ml, 0.971 mol, 1.2 eq.). At the end of the addition, the reaction mixture was allowed to reach room temperature before being poured into ice/H2O (500 ml) and acidified with concentrated HCl. The water phase was extracted with diethyl ether (300 ml) and the combined organic phases were washed with water (400 ml) and aqueous saturated NaCl solution (500 ml), dried (50 g MgSO4) and the solvent evaporated to give the crude 1-isobutylcyclohexanol (148 g).

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