Acrylonitrile → HCID 15550234, compound

HRID 651428Notes

Reaction equation

HRID 651428 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Cl:10])[N:3]=1.C(N(CC)CC)C.C1COCC1.[C:23](#[N:26])[CH:24]=[CH2:25]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH2:25][CH2:24][C:23]#[N:26])[CH:5]=[C:4]([Cl:10])[N:3]=1

Participants

6

Reactant 4

HCID 7855AcrylonitrileHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2794840(2,6-Dichloropyridin-4-yl)methanol

Product 1

HCID 15550234HCID 15550234, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

0.36 g of 2,6-dichloro-4-pyridinemethanol and 0.1 g of triethylamine were dissolved into 2 ml of THF, 0.12 g of acrylonitrile were added to the solution at room temperature, and stirring was conducted for 2 hours. After the reacted solution was left overnight at room temperature, ethyl acetate was added. The organic phase was washed with water, and was dried by adding sodium sulfate. The solvent was removed by evaporation, and the residue was purified by silica gel column chromatography to obtain 0.23 g of 2,6-dichloro-4-(2-cyanoethoxymethyl)pyridine (Compound No. 6).

Workup

  1. additionwere added to the solution at room temperature
  2. waitAfter the reacted solution was left overnight at room temperature
  3. washThe organic phase was washed with water
  4. customwas dried
  5. additionby adding sodium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4f15250c5dae4212b559b53a7254eb25
Source dataset
uspto-grants-2001_08
Patent number
US06281231B1

Reaction notes

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