反応 #2146730

反応方程式

cyclohexanone

HCl

tert-butyllithium

pentane

isobutyl iodide

→

1-isobutylcyclohexanol

溶媒

diethyl ether

反応条件

後処理

1. 1
   温度warmed to 10° C.
2. 2
   温度cooled to −70° C.
3. 3
   workup.ADDITIONAt the end of the addition
4. 4
   その他to reach room temperature
5. 5
   抽出The water phase was extracted with diethyl ether (300 ml)
6. 6
   洗浄the combined organic phases were washed with water (400 ml) and aqueous saturated NaCl solution (500 ml)
7. 7
   乾燥dried (50 g MgSO4)
8. 8
   その他the solvent evaporated

実験手順

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).

出典