反応 #8807

反応方程式

EtOAc

5-isoquinolinecarboxaldehyde

4-bromo-1,2-(methylendioxy)benzene

lithium diisopropylamide

→

title compound

収率 65.0%

α-(5-BRomo-1,3-benzodioxol-4-yl)-5-isoquinolinemethanol

収率 65.0%

溶媒

—

Hexanes

THF

THF

反応条件

後処理

1. 1
   その他A brown solution was formed
2. 2
   workup.STIRRINGThe resulting mixture was stirred at −78° C. for 10 minutes
3. 3
   温度warmed to room temperature
4. 4
   workup.STIRRINGStirring
5. 5
   workup.WAITwas continued for 30 minutes at room temperature
6. 6
   その他the mixture was quenched with saturated NH4Cl solution
7. 7
   抽出The product was extracted with EtOAc
8. 8
   その他the solvent was removed under reduced pressure

実験手順

To a solution of 4-bromo-1,2-(methylendioxy)benzene (3.01 g, 15 mmol) in THF (20 mL) at −78° C. was added dropwise lithium diisopropylamide (10.6 mL of 1.5 M in cyclohexane, 16 mmol). The reaction mixture was stirred at −78° C. under argon for 20 minutes. A brown solution was formed. A solution of 5-isoquinolinecarboxaldehyde (1.90 g, 12 mmol) in THF (4 mL) was added dropwise. The resulting mixture was stirred at −78° C. for 10 minutes and warmed to room temperature. Stirring was continued for 30 minutes at room temperature, and then the mixture was quenched with saturated NH4Cl solution. The product was extracted with EtOAc and the solvent was removed under reduced pressure. Chromatography (SiO2 Type-H, 35% EtOAc in Hexanes) of the residue yielded the title compound as a yellow solid (2.8 g, 7.8 mmol, 65% yield): mp 173–175° C.;

出典