反応 #1605783

反応方程式

NH4Cl

THF

lithium diisopropylamide

THF

hexane

Cyclohexanone

→

solid

収率 80.7%

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

収率 80.7%

反応条件

後処理

1. 1
   温度maintaining the reaction temperature below −65° C
2. 2
   その他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
   抽出was extracted with ethyl acetate (4×200 mL)
8. 8
   洗浄Combined ethyl acetate layer was washed with water (3×100 mL), brine (1×10 mL)
9. 9
   乾燥dried (Na2SO4)
10. 10
    その他Ethyl acetate was evaporated in vacuo
11. 11
    その他to give colorless solid
12. 12
    ろ過The precipitate was filtered
13. 13
    洗浄washed with hexane
14. 14
    その他dried in vacuo

実験手順

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.

出典