Hydrochloric Acid → 1-[[4-(2-Hydroxyethyl)phenyl]methyl]cyclohexanecarbonitrile

HRID 274123

반응식

HRID 274123 반응식
C(NC(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].CN1CCN(C)[C:15]1=[O:20].[CH:21]1([C:27]#[N:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.Cl.[CH3:30][CH2:31][CH2:32][CH2:33]CC>O1CCCC1.O>[OH:20][CH2:15][CH2:11][C:10]1[CH:30]=[CH:31][C:32]([CH2:33][C:21]2([C:27]#[N:28])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:8][CH:9]=1

참가 물질

9

반응물 6

HCID 313Hydrochloric AcidHCID 66611,3-Dimethyl-2-imidazolidinoneHCID 7912DiisopropylamineHCID 8058HexaneHCID 69834CyanocyclohexaneHCID 178418339Butyllithium

생성물 1

HCID 189996321-[[4-(2-Hydroxyethyl)phenyl]methyl]cyclohexanecarbonitrile수율 61.6%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

To a mixture maintained under nitrogen, of 5.6 g (54.9 mmoles) of diisopropylamine and 92 ml of dry tetrahydrofuran, cooled to -40° C., there is added dropwise 34.2 ml (54.7 mmoles) of a 1.6M solution of n-butyllithium in hexane, then 8.2 g of 1,3-dimethylimidazolidin-2-one. The mixture is thereafter cooled to -78° C. and is stirred 1/4 hour before adding 5.45 g (50 mmoles) of commercial cyclohexanecarbonitrile in solution in 82 ml of dry tetrahydrofuran. After having stirred 1 hour, at -78° C., 14.3 g (50 mmoles) of the compound prepared in example 26a is added. The temperature is kept for an additional 3 hours at -78° C., before being allowed to rise and the mixture is stirred 19 hours at room temperature. Waster is then added, the mixture is acidified with HCl and is stirred again for 1 hour, before diluting it with water and extracting the reaction mixture with ether. The organic phase, washed with water, dried over Na2SO4 is concentrated. The liquid obtained is purified by distillation to give 7.5 g (yield= 61.6%) of a yellow liquid. b.p.0.5 =130°-80° C.

후처리

  1. temperatureThe mixture is thereafter cooled to -78° C.
  2. stirringAfter having stirred 1 hour, at -78° C.
  3. stirringthe mixture is stirred 19 hours at room temperature
  4. additionWaster is then added
  5. stirringis stirred again for 1 hour
  6. extractionextracting the reaction mixture with ether
  7. washThe organic phase, washed with water
  8. dry with materialdried over Na2SO4
  9. concentrationis concentrated
  10. customThe liquid obtained
  11. distillationis purified by distillation

출처 및 근거

ORD 기록
ord-e79af58b3a7a4b2a9d3bbdca7fcce1a1
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387709

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