반응 #586115

반응 방정식

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

수율 67.0%

용매

THF

반응 조건

후처리

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

실험 절차

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.).

출처