Ethyl Acetate → Methyl 2-(5-cyano-3-pyridyloxy)butyrate

HRID 1374911Notes

Reaction equation

HRID 1374911 reaction equation
Br[C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:14][CH3:15])[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[N:6][CH:7]=1.[Cu][C:17]#[N:18].C(OCC)(=O)C>CN1CCCC1=O.O>[C:17]([C:2]1[CH:3]=[C:4]([O:8][CH:9]([CH2:14][CH3:15])[C:10]([O:12][CH3:13])=[O:11])[CH:5]=[N:6][CH:7]=1)#[N:18]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 210784362-(5-Bromo-pyridin-3-yloxy)-butyric acid methyl esterHCID 178418546HCID 178418546, compound

Product 1

HCID 21078439Methyl 2-(5-cyano-3-pyridyloxy)butyrate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of methyl 2-(5-bromo-3-pyridyloxy)butyrate (1.37 g) and copper (1) cyanide (0.67 g) in dry N-methylpyrollidin-2-one (5 ml) was stirred at 150° C. under an atmosphere of nitrogen for 3.25 hours then cooled to ambient temperature and stored for 18 hours. The mixture was diluted with water and extracted with ethyl acetate (four times). The extracts were combined, washed with water (three times), dried over magnesium sulphate and evaporated under reduced pressure to give a liquid which was fractionated by chromatography (silica; ethyl acetate) to give the required product, 0.29 g, as an orange oil.

Workup

  1. extractionextracted with ethyl acetate (four times)
  2. washwashed with water (three times)
  3. dry with materialdried over magnesium sulphate
  4. customevaporated under reduced pressure
  5. customto give a liquid which

Sources & evidence

ORD record
ord-b26be1ec0eef4e7b8ef103fc7494862e
Source dataset
uspto-grants-2007_01
Patent number
US07166621B2

Reaction notes

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