تفاعل #2254206

معادلة التفاعل

tetrahydro-2,2-dimethyl-4H-pyran-4-one

n-BuLi

4-bromo-toluene

→

2,2-dimethyl-4-(4-methylphenyl)oxan-4-ol

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe resulting mixture was stirred at −78° C. for another 20 min
2. 2
   أخرىquenched
3. 3
   workup.ADDITIONby adding MeOH (10 ml)
4. 4
   تركيزThe reaction was concentrated under vacuum
5. 5
   workup.ADDITIONthe resulting residue was diluted with EtOAc (500 ml)
6. 6
   غسيلwashed with sat. NH4Cl (250 ml), brine (250 ml)
7. 7
   أخرىdried
8. 8
   تركيزconcentrated

الإجراء التجريبي

n-BuLi (26.3 ml, 1.6 M in hexane, 42 mmol) was added dropwise to a solution of 4-bromo-toluene (7.70 g, 45 mmol) in THF (100 ml) at −78° C. under N2. The resulting mixture was stirred at −78° C. for 30 min and a solution of tetrahydro-2,2-dimethyl-4H-pyran-4-one (3.84 g, 30 mmol) in THF (20 ml) was added. The resulting mixture was stirred at −78° C. for another 20 min and quenched by adding MeOH (10 ml). The reaction was concentrated under vacuum and the resulting residue was diluted with EtOAc (500 ml) and washed with sat. NH4Cl (250 ml), brine (250 ml), dried and concentrated to give 2,2-dimethyl-4-(4-methylphenyl)oxan-4-ol as a white solid, which was used without further purification (5.41 g, 82%).

المصدر