反应详情

A suspension of 14.8 g of ethyltriphenylphosphonium bromide in 150 ml of t-butyl methyl ether was treated with 4.54 g of solid potassium t-butylate at -10° C. within 5 minutes while gassing with argon in a sulphonation flask provided with a mechanical stirrer. The suspension was stirred at room temperature for 1 hour, then treated dropwise at 0° C. within 5 minutes with a solution of 6.4 g of 3-[trans-4-(p-cyanophenyl)cyclohexyl]propionaldehyde in 40 ml of t-butyl methyl ether and stirred at room temperature for a further 15 hours. The mixture was subsequently partitioned three times in diethyl ether/water. The organic extracts were washed twice with water, dried over magnesium sulphate, filtered and concentrated. In order to separate triphenylphosphine oxide, the residue was dissolved in ethyl acetate and the solution was diluted with petroleum ether, filtered and concentrated. Chromatographic separation of the resulting, yellowish oil (8.55 g) on silica gel with ethyl acetate/petroleum ether (vol. 3:97) gave 5.93 g (89%) of p-[trans-4-(3-pentenyl)cyclohexyl]benzonitrile as white crystals.

1. customwhile gassing with argon in a sulphonation flask
2. customprovided with a mechanical stirrer
3. stirringstirred at room temperature for a further 15 hours
4. customThe mixture was subsequently partitioned three times in diethyl ether/water
5. washThe organic extracts were washed twice with water
6. dry with materialdried over magnesium sulphate
7. filtrationfiltered
8. concentrationconcentrated
9. customIn order to separate triphenylphosphine oxide
10. dissolutionthe residue was dissolved in ethyl acetate
11. additionthe solution was diluted with petroleum ether
12. filtrationfiltered
13. concentrationconcentrated
14. customChromatographic separation of the resulting, yellowish oil (8.55 g) on silica gel with ethyl acetate/petroleum ether (vol. 3:97)