反应 #1605783

反应方程式

NH4Cl

THF

lithium diisopropylamide

THF

hexane

Cyclohexanone

→

solid

收率 80.7%

1-[cyano-(4-methoxyphenyl)methyl]cyclohexanol

收率 80.7%

反应条件

后处理

1. 1
   温度maintaining the reaction temperature below −65° C
2. 2
   其他did not rise above −65° C
3. 3
   workup.ADDITIONAfter the addition reaction
4. 4
   workup.STIRRINGwas stirred at −78° C. for 2 hours
5. 5
   workup.ADDITIONcontaining ice
6. 6
   workup.STIRRINGThe mixture was stirred for 15 minutes
7. 7
   萃取was extracted with ethyl acetate (4×200 mL)
8. 8
   洗涤Combined ethyl acetate layer was washed with water (3×100 mL), brine (1×10 mL)
9. 9
   干燥dried (Na2SO4)
10. 10
    其他Ethyl acetate was evaporated in vacuo
11. 11
    其他to give colorless solid
12. 12
    过滤The precipitate was filtered
13. 13
    洗涤washed with hexane
14. 14
    其他dried in vacuo

实验过程

A solution of 4-methoxybenzylnitrile (53.5 g, 0.36 mol) in 400 mL THF was cooled to −78° C. followed by slow addition of a 2.0 M THF solution of lithium diisopropylamide (200 nm, 0.40 mol) maintaining the reaction temperature below −65° C. The reaction was stirred at −78° C. for 30 minutes. Cyclohexanone (39.5 g, 0.40 mol) was added at a rate such that the reaction temperature did not rise above −65° C. After the addition reaction was stirred at −78° C. for 2 hours, then was poured into 1 L saturated aqueous NH4Cl containing ice. The mixture was stirred for 15 minutes and was extracted with ethyl acetate (4×200 mL). Combined ethyl acetate layer was washed with water (3×100 mL), brine (1×10 mL) and dried (Na2SO4). Ethyl acetate was evaporated in vacuo to give colorless solid that was trichurated with hexane. The precipitate was filtered, washed with hexane, dried in vacuo to give colorless solid (72.0 g, 80.7% yield). 1H (CDCl3): 7.30 and 6.90 (q, 4H), 3.80 (s, 3H), 3.75 (s, 1H), 1.55 (m, 10H); 13C (CDCl3): 159.8, 130.8, 123.8, 120.0, 114.1, 72.9, 55.5, 49.5, 34.9, 25.3, 21.6.

来源