m-Formylbenzonitrile → HCID 19002915, compound

HRID 2259516Notes

Reaction equation

HRID 2259516 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=[O:7])#[N:2].[CH:11]([Mg]Br)=[CH2:12].C([O-])(=O)C.[NH4+]>C1COCC1>[OH:7][CH:6]([C:5]1[CH:4]=[C:3]([CH:10]=[CH:9][CH:8]=1)[C:1]#[N:2])[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 90670m-FormylbenzonitrileHCID 517165Ammonium AcetateHCID 178418507HCID 178418507, compound

Product 1

HCID 19002915HCID 19002915, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 3-cyanobenzaldehyde (25 g, 0.190 mmol) in THF (576 mL) was added dropwise at -10° C. vinyl magnesium bromide in THF (202 mL, 0.201 mmol). After 15 min, the reaction mixture was poured on cold 25% aqueous ammonium acetate solution and extracted with EtOAc. The resulting mixture was purified by flash chromatography to provide 17.5 g (60%) of the title product.

Workup

  1. extractionextracted with EtOAc
  2. customThe resulting mixture was purified by flash chromatography

Sources & evidence

ORD record
ord-b7f0eaab8bbd4fe28b47e09640d9bff7
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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