2-(Trimethylsilyl)ethanol → 3-(2-(Trimethylsilyl)ethoxy)isonicotinonitrile

HRID 1972151Notes

Reaction equation

HRID 1972151 reaction equation
[CH3:1][Si:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:11]1[CH:18]=[N:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14].[Cl-].[NH4+]>C1COCC1>[CH3:1][Si:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][O:5][C:11]1[CH:18]=[N:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14]

Participants

6

Reactant 4

HCID 180132-(Trimethylsilyl)ethanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 106783063-Chloropyridine-4-carbonitrile

Product 1

HCID 666177473-(2-(Trimethylsilyl)ethoxy)isonicotinonitrileYield 81.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A flask was charged with 2-(trimethylsilyl)ethanol (1.02 g, 8.66 mmol) and added THF (20 mL). Sodium hydride (0.219 g, 8.66 mmol) was added and the reaction was stirred at ambient temperature for 1 hour. 3-Chloroisonicotinonitrile (1.00 g, 7.22 mmol) was added, and the reaction mixture was stirred at ambient temperature for 1 hour and then at 50° C. overnight. A saturated solution of ammonium chloride was added. The reaction mixture was extracted with ethyl acetate, dried and concentrated to give the desired product (1.30 g, 81.7% yield) as light brown semi solid material.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 1 hour
  2. customat 50° C.
  3. customovernight
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c1c406fe163d4caba6d1617c99e66135
Source dataset
uspto-grants-2013_04
Patent number
US08431713B2

Reaction notes

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