反応 #324917

反応方程式

4,4-dimethyl-cyclohexanone

4-benzyloxybromobenzene

magnesium

→

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

収率 50.1%

溶媒

THF

THF

THF

反応条件

後処理

1. 1
   その他In a 250 mL round-bottomed flask was placed
2. 2
   温度To 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
   その他was removed under reduced pressure
5. 5
   その他The residue was partitioned between EtOAc/saturated NH4Cl
6. 6
   抽出The mixture was extracted twice with EtOAc
7. 7
   乾燥dried (Na2SO4)
8. 8
   濃縮concentrated
9. 9
   その他The residue was purified via column chromatography on silica gel (eluting with 10-40% ethyl acetate/hexanes)

実験手順

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.

出典