Sodium Hydroxide → HCID 68616364, compound

HRID 730063Notes

Reaction equation

HRID 730063 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]#[N:10])=[N:6][CH:7]=1.Br[CH2:12][CH2:13][O:14][CH2:15][CH2:16]Br.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.[Cl-].[NH4+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:9]#[N:10])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21521Bis(2-bromoethyl) etherHCID 29927881(5-Bromopyridin-2-yl)acetonitrile

Product 1

HCID 68616364HCID 68616364, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 5-bromo-2-pyridineacetonitrile (400 mg), triethylbenzylammonium chloride (462 mg), bis(2-bromoethyl)ether (281 μL), and 50% sodium hydroxide solution (10 mL) was stirred at 70° C. for 1 hour. After decantation of aqueous layer, the residue was diluted with saturated ammonium chloride solution and extracted with ethyl acetate. The organic extracts were dried over anhydrous magnesium sulfate, filtered, and then concentrated in vacuo. Flash chromatography (silica, hexane:ethyl acetate=7:3) of the residue gave 5-bromo-2-(4-cyanotetrahydropyran-4-yl)pyridine (104 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-075054c649cd4fef9dfcf99662af4db4
Source dataset
uspto-grants-2009_09
Patent number
US07582659B2

Reaction notes

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