Sodium hydride → HCID 58047200, compound

HRID 1888755Notes

Reaction equation

HRID 1888755 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].[F:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](F)[N:10]=1>C1COCC1>[CH:1]1([CH2:4][O:5][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([F:8])[N:10]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 739342,6-DifluoropyridineHCID 75644Cyclopropanemethanol

Product 1

HCID 58047200HCID 58047200, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cyclopropylmethanol (3.87 g, 47.7 mmol) in THF (50 mL) was added sodium hydride (oil, 60%, 2.08 g, 52.1 mmol), and the mixture was stirred at room temperature for 20 min. To this solution was added 2,6-difluoropyridine (5.00 g, 43.4 mmol) and the mixture was stirred at room temperature for 30 min. The reaction was quenched with water, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1 to 4:1) to give the title compound (5.69 g, yield 78%) as an oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. customThe reaction was quenched with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1 to 4:1)

Sources & evidence

ORD record
ord-4bee40bcb58644c2a709c96064213272
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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