Réaction #586115

Équation de réaction

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

Rendement 67.0%

Solvants

THF

Conditions de réaction

Traitement

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

Mode opératoire

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.).

Source