反应 #586115

反应方程式

hydrochloric acid

tert-butyllithium

3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-1-ol

dimethylformamide

→

4-Hydroxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbaldehyde

收率 67.0%

溶剂

THF

反应条件

后处理

1. 1
   温度The mixture is warmed to room temperature
2. 2
   萃取extracted with ethyl acetate
3. 3
   其他The residue obtained
4. 4
   其他is then purified by chromatography (eluent: 9/1 heptane/ethyl acetate)
5. 5
   其他A white solid is obtained (m=16.5 g; yield=67%; m.p.=144° C.)

实验过程

30 g (106 mmol) of 3-bromo-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-1-ol are dissolved in 500 mL of anhydrous THF. The medium is cooled to −78° C. and 156 mL (265 mmol) of tert-butyllithium are then added dropwise. After 45 minutes at this temperature, 12.3 mL (159 mmol) of dimethylformamide are added. The mixture is warmed to room temperature and then treated with 1N hydrochloric acid solution and extracted with ethyl acetate. The residue obtained is then purified by chromatography (eluent: 9/1 heptane/ethyl acetate). A white solid is obtained (m=16.5 g; yield=67%; m.p.=144° C.).

来源