Reacción #586115

Ecuación de reacción

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

Rendimiento 67.0%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.).

Fuente