تفاعل #586115

معادلة التفاعل

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

المردود 67.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mixture is warmed to room temperature
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   أخرىThe residue obtained
4. 4
   أخرىis then purified by chromatography (eluent: 9/1 heptane/ethyl acetate)
5. 5
   أخرىA white solid is obtained (m=16.5 g; yield=67%; m.p.=144° C.)

الإجراء التجريبي

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.).

المصدر