반응 #1605783

반응 방정식

NH4Cl

THF

lithium diisopropylamide

THF

hexane

Cyclohexanone

→

solid

수율 80.7%

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

수율 80.7%

반응 조건

후처리

1. 1
   온도maintaining the reaction temperature below −65° C
2. 2
   기타did 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
   추출was extracted with ethyl acetate (4×200 mL)
8. 8
   세척Combined ethyl acetate layer was washed with water (3×100 mL), brine (1×10 mL)
9. 9
   건조dried (Na2SO4)
10. 10
    기타Ethyl acetate was evaporated in vacuo
11. 11
    기타to give colorless solid
12. 12
    여과The precipitate was filtered
13. 13
    세척washed with hexane
14. 14
    기타dried in vacuo

실험 절차

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.

출처