Réaction #324917

Équation de réaction

4,4-dimethyl-cyclohexanone

4-benzyloxybromobenzene

magnesium

→

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

Rendement 50.1%

Solvants

THF

THF

THF

Conditions de réaction

Traitement

1. 1
   AutreIn a 250 mL round-bottomed flask was placed
2. 2
   TempératureTo 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
   Autrewas removed under reduced pressure
5. 5
   AutreThe residue was partitioned between EtOAc/saturated NH4Cl
6. 6
   ExtractionThe mixture was extracted twice with EtOAc
7. 7
   Séchagedried (Na2SO4)
8. 8
   Concentrationconcentrated
9. 9
   AutreThe residue was purified via column chromatography on silica gel (eluting with 10-40% ethyl acetate/hexanes)

Mode opératoire

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.

Source