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

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.

1. customThe reaction was quenched
2. additionby adding water (5 mL)
3. extractionextracted with ethyl acetate (3×25 mL)
4. washThe organic layer was washed with brine (10 mL)
5. dry with materialdried with MgSO4
6. customthe solvent was removed by distillation
7. customThe crude material was purified by silicagel chromatography

ORDレコード

ord-1b0e8d298ae64c8b9df10e43febd3af1

出典データセット

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05728846