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

HRID 509198

Reaction equation

HRID 509198 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-7ca49ce3fa9240128628c1b8a5e5f603
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Linked notes

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