Diethyl Ether → 2-(2,2-Dimethoxyethyl)nicotinonitrile

HRID 2358827Notes

Reaction equation

HRID 2358827 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[N:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].[CH3:15][O-:16].[Na+].CC[O:20][CH2:21]C>CO>[CH3:15][O:16][CH:3]([O:20][CH3:21])[CH2:4][C:5]1[N:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10942334Sodium MethoxideHCID 134111132-((Trimethylsilyl)ethynyl)nicotinonitrile

Product 1

HCID 134111172-(2,2-Dimethoxyethyl)nicotinonitrileYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 228a (1.62 g, 8.09 mmol) was reacted with sodium methoxide as a 25 wt % solution (8.74 g, 40.4 mmol) in methanol (5 mL) for two hours at 80° C. The crude product was isolated by extraction with ether, dried over MgSO4, filtered and concentrated under vacuum to give the title compound (1.46 g, 94%) sufficiently pure for use as isolated.

Workup

  1. dry with materialdried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-6e525e88f5564ebcbd2890cf21860859
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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