Acrylonitrile → HCID 68292301, compound

HRID 1504963Notes

Reaction equation

HRID 1504963 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12])=[N:8][CH:9]=1)([O-:3])=[O:2].[C:19](#[N:22])[CH:20]=[CH2:21].CO[Na]>CO>[C:19]([CH2:20][CH2:21][C:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1)([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12])#[N:22]

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 2764544HCID 2764544, compoundHCID 178418582HCID 178418582, compound

Product 1

HCID 68292301HCID 68292301, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 75 (10.5 g, 41 mmol) and acrylonitrile (17.4 g, 328 mmol) in absolute CH3OH (100 mL) was added a catalytic amount of CH3ONa (216 mg, 4 mmol) at room temperature with stirring under N2. The mixture was stirred at room temperature for 10 h under N2. The mixture was diluted with aqNaHCO3 and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, concentrated and purified with silica gel column chromatography (PE:EtOAc=5:1) to give compound 76 (3.3 g, 20%) as a light yellow oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 10 h under N2
  2. additionThe mixture was diluted with aqNaHCO3
  3. extractionextracted with DCM
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified with silica gel column chromatography (PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-af0707846eda4e4b8a1cc0f479cbdd6d
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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