Реакция #324917

Уравнение реакции

4,4-dimethyl-cyclohexanone

4-benzyloxybromobenzene

magnesium

→

1-(4-benzyloxy-phenyl)-4,4-dimethylcyclohexanol

Выход 50.1%

Растворители

THF

THF

THF

Условия реакции

Обработка

1. 1
   ДругоеIn a 250 mL round-bottomed flask was placed
2. 2
   ТемператураTo the slurry, cooled in an ice-water bath
3. 3
   workup.STIRRINGThe reaction mixture was stirred for 1 hour at room temperature after which the solvent
4. 4
   Другоеwas removed under reduced pressure
5. 5
   ДругоеThe residue was partitioned between EtOAc/saturated NH4Cl
6. 6
   ЭкстракцияThe mixture was extracted twice with EtOAc
7. 7
   Сушкаdried (Na2SO4)
8. 8
   Концентрированиеconcentrated
9. 9
   ДругоеThe residue was purified via column chromatography on silica gel (eluting with 10-40% ethyl acetate/hexanes)

Методика

In a 250 mL round-bottomed flask was placed magnesium turnings (1.85 g, 76.1 mmol), which were stirred under vacuum without solvent overnight. To the turnings was added anhydrous THF (10 mL) and 4-benzyloxybromobenzene (10.0 g, 38.0 mmol) in anhydrous THF (40 ml) over 15 min. After the reaction was complete, the resulting gray slurry was stirred for 2 h at 60° C. To the slurry, cooled in an ice-water bath, was added 4,4-dimethyl-cyclohexanone (3.36 g, 26.6 mmol) in THF (15 mL). The reaction mixture was stirred for 1 hour at room temperature after which the solvent was removed under reduced pressure. The residue was partitioned between EtOAc/saturated NH4Cl. The mixture was extracted twice with EtOAc. The organic phases were combined, dried (Na2SO4) and concentrated. The residue was purified via column chromatography on silica gel (eluting with 10-40% ethyl acetate/hexanes) to give 4.14 g (50%) of 1-(4-benzyloxy-phenyl)-4,4-dimethylcyclohexanol.

Источник