Ethanol → (5-Cyano-2-pyridinyl)methylacetate

HRID 639148Notes

Reaction equation

HRID 639148 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].CC1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][N+:10]=1[O-].C(O)C.C(=O)(O)[O-].[Na+]>CS(C)=O>[C:13]([C:12]1[CH:15]=[CH:16][C:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])=[N:10][CH:11]=1)#[N:14]

Participants

6

Reactant 4

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 198186716-Methylpyridine-3-carbonitrile 1-oxide

Product 1

HCID 67557567(5-Cyano-2-pyridinyl)methylacetate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Acetic anhydride (3.2 g, 31.31 mmol) is heated to 115° C. under an argon atmosphere. The compound of Example 30A (700 mg, 5.22 mmol) is added and the solution is stirred at reflux for one hour. Ethanol (3 ml, 51.12 mmol) is added dropwise to the mixture and refluxing is continued for 10 minutes. The mixture is cooled to room temperature, poured into ice water and neutralised with saturated sodium bicarbonate solution. The aqueous phase is extracted with diethyl ether. The organic phase is washed with brine, dried with magnesium sulphate, filtered and concentrated in vacuo to afford a black oil. The oil is dissolved in dimethylsulfoxide (8 ml) and purified by preparative HPLC.

Workup

  1. temperatureat reflux for one hour
  2. temperaturerefluxing
  3. extractionThe aqueous phase is extracted with diethyl ether
  4. washThe organic phase is washed with brine
  5. dry with materialdried with magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a black oil
  9. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-eea6645f048f443eac92dcf4c10d39e2
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

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