反応 #2254206

反応方程式

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

n-BuLi

4-bromo-toluene

→

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

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe resulting mixture was stirred at −78° C. for another 20 min
2. 2
   その他quenched
3. 3
   workup.ADDITIONby adding MeOH (10 ml)
4. 4
   濃縮The reaction was concentrated under vacuum
5. 5
   workup.ADDITIONthe resulting residue was diluted with EtOAc (500 ml)
6. 6
   洗浄washed with sat. NH4Cl (250 ml), brine (250 ml)
7. 7
   その他dried
8. 8
   濃縮concentrated

実験手順

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%).

出典