反应详情

温度

0 °C

To a suspension of 3.69 g (123 mmol) of 80% sodium hydride in 150 mL of anhydrous tetrahydrofuran and 11.6 g (115 mmol) of diisopropylamine, at 0° C. was added 12.82 g (112 mmol) of cyclopentanecarboxylic acid. This was then heated at reflux for 15 minutes, cooled to 0° C. and 45 mL of 2.5M n-butyllithium in hexane added. After 15 minutes at 0° C. and 30 minutes at 35° C., the mixture was recooled to 0° C. and a solution of 14.4 g (112 mmol) of 4-chloromethylpyridine (freshly prepared from 4-chloromethylpyridine hydrochloride by neutralization with aqueous sodium bicarbonate, extraction with hexane, drying and concentrating) was added. After 30 minutes at 0° C. and 60 minutes at 35° C., the mixture was cooled to 0° C., water carefully added and extracted twice with diethyl ether. The aqueous layer was acidified to pH 3 with 6N hydrochloric acid whereupon a precipitate formed. The pH was adjusted to 5.9 with 10% sodium hydroxide and the solids collected. Recrystallization from hot ethanol and hexane afforded 5.7 g of desired product, m/e 206 (M+H).

1. temperatureThis was then heated
2. temperatureat reflux for 15 minutes
3. custom30 minutes
4. customat 35° C.
5. customwas recooled to 0° C.
6. customdrying
7. concentrationconcentrating)
8. additionwas added
9. waitAfter 30 minutes at 0° C.
10. temperature60 minutes at 35° C., the mixture was cooled to 0° C.
11. additionwater carefully added
12. extractionextracted twice with diethyl ether
13. customformed
14. customthe solids collected
15. customRecrystallization from hot ethanol and hexane