Реакция #586115

Уравнение реакции

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

Выход 67.0%

Растворители

THF

Условия реакции

Обработка

1. 1
   ТемператураThe mixture is warmed to room temperature
2. 2
   Экстракцияextracted with ethyl acetate
3. 3
   ДругоеThe residue obtained
4. 4
   Другоеis then purified by chromatography (eluent: 9/1 heptane/ethyl acetate)
5. 5
   ДругоеA white solid is obtained (m=16.5 g; yield=67%; m.p.=144° C.)

Методика

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.).

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