Water → 959616-50-3

HRID 385550Notes

Reaction equation

HRID 385550 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][O:10]COC)[C:5]([CH3:8])=[N:6][CH:7]=1.O.[OH-].[Na+].C(=O)([O-])O.[Na+]>O1CCOCC1.Cl.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[C:5]([CH3:8])=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 57815501HCID 57815501, compound

Product 1

HCID 57815512959616-50-3Yield 109.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of 0.49 g of 5-fluoro-3-((methoxymethoxy)methyl)-2-methylpyridine in 20 mL of dioxane, 10 mL of 6.0 mol/L hydrochloric acid was added, and the mixture was stirred at 30 to 40° C. for 1 hour. Thereto were added water and ethyl acetate, and the mixture was adjusted to pH 5.5 with a 20% aqueous sodium hydroxide solution and a saturated aqueous sodium hydrogen carbonate solution. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate twice. 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 0.41 g of (5-fluoro-2-methylpyridin-3-yl)methanol as a light yellow oily substance.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate twice
  3. washthe resultant solution was washed with water
  4. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-031394552eb64b618a5aa9776fe523d4
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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