Reacción #1605783

Ecuación de reacción

NH4Cl

THF

lithium diisopropylamide

THF

hexane

Cyclohexanone

→

solid

Rendimiento 80.7%

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

Rendimiento 80.7%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturamaintaining the reaction temperature below −65° C
2. 2
   Otrodid 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
   Extracciónwas extracted with ethyl acetate (4×200 mL)
8. 8
   LavadoCombined ethyl acetate layer was washed with water (3×100 mL), brine (1×10 mL)
9. 9
   Secadodried (Na2SO4)
10. 10
    OtroEthyl acetate was evaporated in vacuo
11. 11
    Otroto give colorless solid
12. 12
    FiltraciónThe precipitate was filtered
13. 13
    Lavadowashed with hexane
14. 14
    Otrodried in vacuo

Procedimiento

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.

Fuente