Methanol → 2-(2,2-Dimethoxyethyl)nicotinonitrile

HRID 1772013Notes

Reaction equation

HRID 1772013 reaction equation
C[Si]([C:5]#[C:6][C:7]1[N:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10])(C)C.[CH3:15][O-:16].[Na+].[CH3:18][OH:19]>>[CH3:15][O:16][CH:5]([O:19][CH3:18])[CH2:6][C:7]1[N:14]=[CH:13][CH:12]=[CH:11][C:8]=1[C:9]#[N:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 134111132-((Trimethylsilyl)ethynyl)nicotinonitrile

Product 1

HCID 134111172-(2,2-Dimethoxyethyl)nicotinonitrileYield 75%

Conditions

Temperature
80 °C

Procedure

To a solution of 2-((trimethylsilyl)ethynyl)nicotinonitrile (19.14 g, 95.7 mmol) in MeOH (200 mL) was added sodium methanolate (16.5 g, 306.2 mmol). The reaction mixture was refluxed at 80° C. for 14 h under N2. After removal of the MeOH, the residue was diluted with H2O and extracted with DCM (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography (eluting with DCM) to yield 2-(2,2-dimethoxyethyl)nicotinonitrile as a yellow oil (13.76 g, yield 75%). ESI MS: m/z 193 [M+H]+.

Workup

  1. customAfter removal of the MeOH
  2. additionthe residue was diluted with H2O
  3. extractionextracted with DCM (3×100 mL)
  4. washThe combined organic layers were washed with brine (100 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product
  9. customThe crude product was purified by silica gel column chromatography (eluting with DCM)

Sources & evidence

ORD record
ord-ffc0a2fcd0b64868875dad309c00c159
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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