Phenylacetyl chloride → 3-Oxo-4-phenylbutanenitrile

HRID 1960980Notes

Reaction equation

HRID 1960980 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[Li]CCCC.[C:12]1([CH2:18]C(Cl)=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[O:6]=[C:4]([CH2:18][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][C:1]#[N:2]

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 9740Cyanoacetic acidHCID 178418339Butyllithium

Product 1

HCID 5626663-Oxo-4-phenylbutanenitrileYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cyanoacetic acid (2 g, 23.5 mmol) in THF (100 mL) at −78° C. was added nBuLi (10 mL, 25.9 mmol, 2.5M in hexanes). After 30 min, phenylacetyl chloride (1.6 mL, 11.8 mmol) was added dropwise. Following an additional 30 min, the solution was partitioned between 1N HCl-Et2O and the aqueous phase was washed several times with Et2O. The combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (silica, 30% EtOAc in hexanes) yielding the title compound (770 mg, 40%) as a tan oil: LCMS (ES) m/z 160 (M+H)+.

Workup

  1. waitFollowing an additional 30 min
  2. customthe solution was partitioned between 1N HCl-Et2O
  3. washthe aqueous phase was washed several times with Et2O
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified via column chromatography (silica, 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cadee10fd3b34124a87c47e04302ddbc
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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