Реакция #2006436

Уравнение реакции

1-ethyl-2-methoxycyclohexanol

n-butyllithium

hexane

methacryloyl chloride

→

1-ethyl-2-methoxycyclohexyl methacrylate

Растворители

—

ice water

ether

ether

Условия реакции

Обработка

1. 1
   Другоеequipped with a water condenser, addition funnel and a nitrogen inlet
2. 2
   ТемператураThis solution was cooled in an ice/water bath
3. 3
   Температураheated
4. 4
   Температураto reflux for 30 minutes
5. 5
   ТемператураThe reaction mixture was cooled to room temperature
6. 6
   Другоеquenched with 125 ml of deionized water
7. 7
   ДругоеThe organic phase was separated
8. 8
   Экстракцияthe water phase was extracted with 50 ml ether
9. 9
   ПромывкаThe combined ether solutions were washed with 100 ml brine
10. 10
    Сушкаdried over anhydrous magnesium sulfate
11. 11
    ДругоеThe solvent was removed in a rotary evaporator
12. 12
    Другоеthe crude product was chromatographed on a neutral alumina column

Методика

1-ethyl-2-methoxycyclohexanol from the previous step (10 g, 0.063 mole) in 50 ml ether was placed in a three neck flask equipped with a water condenser, addition funnel and a nitrogen inlet. This solution was cooled in an ice/water bath and n-butyllithium, 1.6 molar in hexane (45 ml, 0.072 mole) was added dropwise. The contents were allowed to warm to room temperature and stirred for 30 minutes. The mixture was cooled again in ice/water bath and methacryloyl chloride (7.31 g, 0.070 mole) in 25 ml ether was added dropwise and heated to reflux for 30 minutes. The reaction mixture was cooled to room temperature and quenched with 125 ml of deionized water. The organic phase was separated and the water phase was extracted with 50 ml ether. The combined ether solutions were washed with 100 ml brine and dried over anhydrous magnesium sulfate. The solvent was removed in a rotary evaporator and the crude product was chromatographed on a neutral alumina column using hexane as elutant. The product was a clear liquid (9.79 g) which was characterized by NMR and IR.

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