反応 #2702

反応方程式

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

溶媒

THF

THF

反応条件

後処理

1. 1
   その他The reaction was quenched
2. 2
   workup.ADDITIONby adding water (5 mL)
3. 3
   抽出extracted with ethyl acetate (3×25 mL)
4. 4
   洗浄The organic layer was washed with brine (10 mL)
5. 5
   乾燥dried with MgSO4
6. 6
   その他the solvent was removed by distillation
7. 7
   その他The crude material was purified by silicagel chromatography

実験手順

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.

出典