Reaktion #1605783
ord-1f41eb12be644d7cb090fee575e8195a
Reaktionsgleichung
Reagenzien
Reaktionsbedingungen
Aufarbeitung
- 1Temperaturmaintaining the reaction temperature below −65° C
- 2Sonstigedid not rise above −65° C
- 3workup.ADDITIONAfter the addition reaction
- 4workup.STIRRINGwas stirred at −78° C. for 2 hours
- 5workup.ADDITIONcontaining ice
- 6workup.STIRRINGThe mixture was stirred for 15 minutes
- 7Extraktionwas extracted with ethyl acetate (4×200 mL)
- 8WaschenCombined ethyl acetate layer was washed with water (3×100 mL), brine (1×10 mL)
- 9Trocknendried (Na2SO4)
- 10SonstigeEthyl acetate was evaporated in vacuo
- 11Sonstigeto give colorless solid
- 12FiltrationThe precipitate was filtered
- 13Waschenwashed with hexane
- 14Sonstigedried in vacuo
Vorschrift
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.