تفاعل #324917

معادلة التفاعل

4,4-dimethyl-cyclohexanone

4-benzyloxybromobenzene

magnesium

→

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

المردود 50.1%

المذيبات

THF

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىIn a 250 mL round-bottomed flask was placed
2. 2
   درجة الحرارةTo 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
   أخرىwas removed under reduced pressure
5. 5
   أخرىThe residue was partitioned between EtOAc/saturated NH4Cl
6. 6
   استخلاصThe mixture was extracted twice with EtOAc
7. 7
   تجفيفdried (Na2SO4)
8. 8
   تركيزconcentrated
9. 9
   أخرىThe residue was purified via column chromatography on silica gel (eluting with 10-40% ethyl acetate/hexanes)

الإجراء التجريبي

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.

المصدر