反応 #586115

反応方程式

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

収率 67.0%

溶媒

THF

反応条件

後処理

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

実験手順

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.).

出典