反应详情

温度

80 °C

1-methoxybicyclo[3.2.2]non-6-en-2,4-dione (0.080 g, 0.044 mmol) stirred in dry chloroform (4 ml) under a nitrogen atmosphere. 4-Dimethylaminopyridine (0.268 g, 2.2 mmol) is added, followed by dry toluene (1 ml) and the mixture is heated to 80° C. To this reaction mixture is then added 4′-chloro-4-methylbiphen-3-yl-lead triacetate (0.400 g, 0.67 mmol) portionwise, over 4 minutes, and the mixture is held at 80° C. for 3¼ hour. The reaction mixture is cooled to room temperature, acidified with dilute aqueous hydrochloric acid (10 ml), stirred vigorously for 10 minutes, then filtered through diatomaceous earth and the filter cake is washed with dichloromethane (10 ml). The filtrate is poured into a separating funnel, the organic layer collected and the aqueous phase is extracted with dichloromethane (2×10 ml). The organic fractions are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under vacuum. The residue is taken up in N,N-dimethylformamide (approximately 2 ml) and purified by preparative reverse-phase HPLC to give 3-(4′-chloro-4-ethylbiphen-3-yl)-1-methoxybicyclo[3.2.2]non-6-ene-2,4-dione.

1. waitthe mixture is held at 80° C. for 3¼ hour
2. temperatureThe reaction mixture is cooled to room temperature
3. filtrationfiltered through diatomaceous earth
4. washthe filter cake is washed with dichloromethane (10 ml)
5. additionThe filtrate is poured into a separating funnel
6. customthe organic layer collected
7. extractionthe aqueous phase is extracted with dichloromethane (2×10 ml)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationthe filtrate is concentrated under vacuum
11. custompurified by preparative reverse-phase HPLC