Sodium Bicarbonate → (5-Fluoro-6-methoxypyridin-3-yl)methanol

HRID 385563Notes

Reaction equation

HRID 385563 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[C:9]([O:18][CH3:19])=[N:10][CH:11]=[C:12]([CH:17]=1)[C:13](OC)=[O:14].C(=O)([O-])O.[Na+]>O1CCCC1>[F:7][C:8]1[CH:17]=[C:12]([CH2:13][OH:14])[CH:11]=[N:10][C:9]=1[O:18][CH3:19]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 46311253Methyl 5-fluoro-6-methoxynicotinate

Product 1

HCID 57815441(5-Fluoro-6-methoxypyridin-3-yl)methanolYield 111.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.24 g of lithium aluminum hydride in 6 mL of tetrahydrofuran, a solution of 0.58 g of methyl 5-fluoro-6-methoxynicotinate in 3.5 mL of tetrahydrofuran was dropped under cooling with ice. After warming to room temperature, the mixture was stirred for 30 minutes. Thereto was dropped a saturated aqueous sodium hydrogen carbonate solution under cooling with ice, after stirring for 10 minutes, the reaction mixture was filtered through celite, and the filtration residue was washed with ethyl acetate and water. The organic layer of the filtrate was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.55 g of (5-fluoro-6-methoxypyridin-3-yl)methanol as a brown oily substance.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. stirringafter stirring for 10 minutes
  4. filtrationthe reaction mixture was filtered through celite
  5. washthe filtration residue was washed with ethyl acetate and water
  6. customThe organic layer of the filtrate was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washthe resultant solution was washed with water
  9. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0706982113ad42619dd254da72fa5a56
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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