Acetone Cyanohydrin → Phenyl(pyridin-3-yl)acetonitrile

HRID 509198

반응식

HRID 509198 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCO[C:23](/[N:25]=N/C(OCC)=O)=O.[C:32]1([CH:38]([C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)O)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CC(C)(O)C#N>C1COCC1>[C:32]1([CH:38]([C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)[C:23]#[N:25])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

참가 물질

6

반응물 4

HCID 6406Acetone CyanohydrinHCID 11776TriphenylphosphineHCID 234839Phenyl(pyridin-3-yl)methanolHCID 5462977Diethyl azodicarboxylate

생성물 1

HCID 270956Phenyl(pyridin-3-yl)acetonitrile수율 52.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of triphenylphosphine (3.83 g, 14.61 mmol) in THF (40 mL) at 0° C. was added DEAD (2.54 g, 14.61 mmol) drop wise and the reaction mixture was stirred for 20 minutes. Compound 76 (1.78 g, 9.61 mmol) was added to the reaction mixture and stirred for an additional 20 minutes. Then acetone cyanohydrin (1.319 mL, 14.42 mmol) was added, stirred for 1 h at 0° C. and 18 h at room temperature. The reaction mixture was concentrated then purified by flash chromatography to afford 77 (0.972 g, 52%).

후처리

  1. stirringstirred for an additional 20 minutes
  2. stirringstirred for 1 h at 0° C. and 18 h at room temperature
  3. concentrationThe reaction mixture was concentrated
  4. customthen purified by flash chromatography

출처 및 근거

ORD 기록
ord-7ca49ce3fa9240128628c1b8a5e5f603
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096565B2

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