反应详情

温度

-78 °C

Treat a −78° C. solution of methyl cyclohexane carboxylate (15.0 g, 0.105 mol) in THF (150 mL) with a 2M solution of lithium diisopropylamide in heptane/THF/ethylbenzene (63.3 mL, 0.126 mol) and stir at −78° C. for 20 minutes under N2. Treat the reaction with bromoacetonitrile (25.31 g, 0.211 mol) and stir at −78° C. for 15 minutes. Warm the reaction to room temperature and stir 4 hours. Acidify the reaction with 1 N HCl and then dilute the reaction with ethyl acetate and wash with water. Dry the organic layer (Na2SO4) and remove the solvent in vacuo to afford crude product. Purify with a 0 to 30% ethyl acetate in hexanes gradient on silica gel to afford 7.78 g (41%) of the titled product. Rf=0.32 (3/1 hexanes/ethyl acetate).

1. additionTreat
2. stirringstir at −78° C. for 15 minutes
3. temperatureWarm
4. customthe reaction to room temperature
5. stirringstir 4 hours
6. additiondilute
7. washwash with water
8. dry with materialDry the organic layer (Na2SO4)
9. customremove the solvent in vacuo
10. customto afford crude product
11. customPurify with a 0 to 30% ethyl acetate in hexanes gradient on silica gel