反应详情

温度

30 °C

6,7-Dichloro-2,3-dihydro-5-methoxy-2-propyl-1H-inden-1-one (13.66 g, 0.05 mole) dissolved in toluene (80 ml) was added over 15 minutes with stirring under N2 to a suspension of 56% sodium hydride (2.36 g, 0.055M) in dimethylformamide (65 ml) and toluene (15 ml) at 25°. The mixture was stirred without external heat for 11/2 hours, at 50° C. for 1/2 hour and then cooled to 30° C. A solution of 1,3-dichloro-2-butene (7.81 g, 0.0625 mole) in toluene (10 ml) was added, and the mixture was heated at 50°-55° for 2 hours, poured into ice water, and extracted with diethyl ether. The organic extracts were washed with water, dried over MgSO4, concentrated under vacuum and chromatographed on silica with elution with 1/1 hexane/methylene chloride to obtain 14.5 g of product as an oil which was a mixture of cis-trans isomers.

1. additionwas added over 15 minutes
2. temperaturewithout external heat for 11/2 hours
3. temperaturethe mixture was heated at 50°-55° for 2 hours
4. extractionextracted with diethyl ether
5. washThe organic extracts were washed with water
6. dry with materialdried over MgSO4
7. concentrationconcentrated under vacuum
8. customchromatographed on silica with elution with 1/1 hexane/methylene chloride