反应详情

温度

0 °C

To a solution of dicyclohexylamine (4.263 g, 23.5 mmol) in THF (10 mL) 1.6 M n-BuLi in hexane (13.23 mL, 21.15 mmol) was added with stirring over 20 min at temperature between −20° C. and −15° C. This orange suspension was stirred 10 min at −20° C. and then warmed up to 0° C. To this orange suspension a solution of cyclohexanecarboxylic acid isopropyl ester (3.0 g, 17.63 mmol) in THF (22 mL) was added over 15 min at 0° C. The resulting solution was stirred 30 min at 0° C., then 1-bromo-2-ethylbutane (4.073 g, 24.7 mmol) in THF (11 mL) was added at the same temperature over 15 min. Stirring at 0° C. was continued overnight and for an additional 2 h at room temperature. At 5° C. cold water (20 mL) was added, followed by 2N HCl (50 mL). The white suspension was filtered and the filter cake was washed with water and ethyl acetate. The organic phase of the filtrate was washed with sat. aq. NaHCO3 and with aq. NaCl. The aqueous phases were extracted with ethyl acetate. The organic phases were combined, dried over sodium sulfate and concentrated. The crude product (4.7 g) was distilled at 50° C. (0.01 mbar) to give 3.95 g (88%) 1-(2-ethyl-butyl)-cyclohexanecarboxylic acid isopropyl ester as colorless oil, purity 97% (GC area).

1. stirringThis orange suspension was stirred 10 min at −20° C.
2. stirringThe resulting solution was stirred 30 min at 0° C.
3. stirringStirring at 0° C.
4. waitwas continued overnight and for an additional 2 h at room temperature
5. filtrationThe white suspension was filtered
6. washthe filter cake was washed with water and ethyl acetate
7. washThe organic phase of the filtrate was washed with sat. aq. NaHCO3 and with aq. NaCl
8. extractionThe aqueous phases were extracted with ethyl acetate
9. dry with materialdried over sodium sulfate
10. concentrationconcentrated
11. distillationThe crude product (4.7 g) was distilled at 50° C. (0.01 mbar)