반응 #2254206

반응 방정식

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

n-BuLi

4-bromo-toluene

→

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

용매

THF

THF

반응 조건

후처리

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

실험 절차

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%).

출처