Water → (3-Butenyl){[5-(1-methyl-1-hydroxyethyl)isoxazol-3-yl]methyl}malononitrile

HRID 2261286Notes

Reaction equation

HRID 2261286 reaction equation
[CH3:1][C:2]([C:5]1[O:9][N:8]=[C:7]([CH2:10][CH:11]([C:14]#[N:15])[C:12]#[N:13])[CH:6]=1)([OH:4])[CH3:3].I[CH2:17][CH2:18][CH:19]=[CH2:20].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:20]([C:11]([CH2:10][C:7]1[CH:6]=[C:5]([C:2]([CH3:1])([OH:4])[CH3:3])[O:9][N:8]=1)([C:12]#[N:13])[C:14]#[N:15])[CH2:19][CH:18]=[CH2:17]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5432164-Iodobut-1-eneHCID 57736354{[5-(1-Methyl-1-hydroxyethyl)isoxazol-3-yl]methyl}malononitrile

Product 1

HCID 86631040(3-Butenyl){[5-(1-methyl-1-hydroxyethyl)isoxazol-3-yl]methyl}malononitrileYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.41 g of {[5-(1-methyl-1-hydroxyethyl)isoxazol-3-yl]methyl}malononitrile and 0.63 g of 4-iodo-1-butene were dissolved in 6 ml of N,N-dimethylformamide, and 0.55 g of potassium carbonate was then added under ice-cooling. The mixture was stirred at room temperature overnight. After water was added, the reaction mixture was extracted with methyl-t-butyl ether. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.43 g of (3-butenyl){[5-(1-methyl-1-hydroxyethyl)isoxazol-3-yl]methyl}malononitrile represented by the following formula:

Workup

  1. temperaturecooling
  2. extractionthe reaction mixture was extracted with methyl-t-butyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-773faf32bc804964829273aa0771d424
Source dataset
uspto-grants-2010_12
Patent number
US07846956B2

Reaction notes

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