반응 #2702

반응 방정식

ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate

n-BuLi

hexane

1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

Compound C

1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

→

title compound

Ethyl 4-[1-(2,2-dimethoxyethyl)-2-{1(tol-4-yl)3,4-dihydro-4,4-dimethylnaphthalen-7-yl}-(E)-ethenyl]-benzoate

용매

THF

THF

반응 조건

후처리

1. 1
   기타The reaction was quenched
2. 2
   workup.ADDITIONby adding water (5 mL)
3. 3
   추출extracted with ethyl acetate (3×25 mL)
4. 4
   세척The organic layer was washed with brine (10 mL)
5. 5
   건조dried with MgSO4
6. 6
   기타the solvent was removed by distillation
7. 7
   기타The crude material was purified by silicagel chromatography

실험 절차

To a cold (-78° C.) solution of ethyl 4-(diethoxyphosphoryl-3,3-dimethoxypropyl)benzoate (Compound D, 350 mg, 0.9 mmol, available in accordance with EPO Application No. 0 210 929 published on Feb. 4, 1987), in THF (9 mL), was added n-BuLi in hexane (1.6M solution, 0.7 mL, 1.1 mmol). The mixture was stirred for 1.5 hours. To this solution 1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde (Compound C, 200 mg, 0.72 mmol), in THF (1 mL) was added and the mixture was gradually warmed to ambient temperature (4 h). The reaction was quenched by adding water (5 mL), and extracted with ethyl acetate (3×25 mL). The organic layer was washed with brine (10 mL), dried with MgSO4 and the solvent was removed by distillation. The crude material was purified by silicagel chromatography to afford the title compound as a colorless off.

출처