Reaktion #2702

Reaktionsgleichung

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

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched
2. 2
   workup.ADDITIONby adding water (5 mL)
3. 3
   Extraktionextracted with ethyl acetate (3×25 mL)
4. 4
   WaschenThe organic layer was washed with brine (10 mL)
5. 5
   Trocknendried with MgSO4
6. 6
   Sonstigethe solvent was removed by distillation
7. 7
   SonstigeThe crude material was purified by silicagel chromatography

Vorschrift

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.

Quelle