Isobutyronitrile → HCID 117760181, compound

HRID 1049569Notes

Reaction equation

HRID 1049569 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[C:13](#[N:17])[CH:14]([CH3:16])[CH3:15].[CH3:18][O:19][CH2:20][O:21][CH2:22][C:23]1[CH:24]=[C:25](/[CH:29]=[CH:30]/[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:26]=[CH:27][CH:28]=1>CCCCCC.C1COCC1.O>[C:13]([C:14]([CH3:16])([CH3:15])[CH:29]([C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([CH2:22][O:21][CH2:20][O:19][CH3:18])[CH:24]=1)[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])#[N:17]

Participants

8

Reactant 4

HCID 6559IsobutyronitrileHCID 7912DiisopropylamineHCID 131736029(E)-ethyl 3-(3-((methoxymethoxy)methyl)phenyl)acrylateHCID 178418339Butyllithium

Product 1

HCID 117760181HCID 117760181, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Under a nitrogen atmosphere, a solution (1.6 M, 1.50 mL) of n-butyllithium in hexane was added to a solution of diisopropylamine (336 μL) in THF (2 mL) at −78° C., to the reaction mixture was added isobutyronitrile (227 μL) at −78° C., and the mixture was stirred for 5 min. To the reaction mixture was added (E)-ethyl 3-(3-((methoxymethoxy)methyl)phenyl)acrylate (250 mg) at −78° C., and the mixture was stirred at room temperature for 20 min. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent of the reaction mixture was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (210 mg) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent of the reaction mixture was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d1c7ee74a99a438fb6094020aa533cb5
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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