Hydracrylonitrile → 1-[(2-Cyanoethoxycarbonyl)methyl]-1-Cyclohexane Acetic Acid

HRID 227341

반응식

HRID 227341 반응식
C([Li])CCC.[OH:6][CH2:7][CH2:8][C:9]#[N:10].[C:11]12([CH2:22][C:21](=[O:23])[O:20][C:18](=[O:19])[CH2:17]1)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2>C1COCC1>[C:9]([CH2:8][CH2:7][O:6][C:21]([CH2:22][C:11]1([CH2:17][C:18]([OH:20])=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:23])#[N:10]

참가 물질

5

반응물 3

HCID 8011HydracrylonitrileHCID 27342891,1-Cyclohexanediacetic AnhydrideHCID 178418339Butyllithium

생성물 1

HCID 223409601-[(2-Cyanoethoxycarbonyl)methyl]-1-Cyclohexane Acetic Acid수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
30 °C

실험 절차

8.2 mL of 1.6M butyllithium was added to a −78° C. solution of 3-hydroxy-propionitrile (13.19 mmol) in 50 mL of THF. The reaction mixture was warmed to 30° C. and stirred for 30 minutes. Then, a solution of 1,1-cyclohexanediacetic anhydride (10.99 mmol) in 10 mL of THF was added dropwise. The reaction mixture was warmed to room temperature over a period of one hour and stirred at room temperature with monitoring by TLC. When the reaction was judged complete, the reaction mixture was quenched with saturated ammonium chloride solution and THF was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate, washed with brine and dried over Na2SO4. After concentration in vacuo the residue was purified on silica gel (5% methanol in dichloromethane) to afford 2.64 g (95%) of the title compound. 1H NMR (CDCl3): δ 4.28 (2H, t, J=6.4 Hz); 2.71 (2H, t, J=6.4 Hz); 2.61 (4H, m); 1.52-1.42 (10H, m).

후처리

  1. temperatureThe reaction mixture was warmed to room temperature over a period of one hour
  2. stirringstirred at room temperature with monitoring by TLC
  3. customthe reaction mixture was quenched with saturated ammonium chloride solution and THF
  4. customwas removed under reduced pressure
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationAfter concentration in vacuo the residue
  9. customwas purified on silica gel (5% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-14a017c53a274a38a7fe18852d35e6ba
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560483B2

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