Water → HCID 59526988, compound

HRID 384468Notes

Reaction equation

HRID 384468 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12](F)[N:11]=1.[H-].[Na+].O>CN(C=O)C>[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:8][CH2:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[N:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 739342,6-DifluoropyridineHCID 2773573(Oxan-4-yl)methanol

Product 1

HCID 59526988HCID 59526988, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tetrahydro-2H-pyran-4-yl methanol (1.00 g) and 2,6-difluoropyridine (1.19 g) in DMF (10 mL) was added 60% sodium hydride (410 mg), and the mixture was stirred at 80° C. for 8 hours. Water (50 mL) was added dropwise to the reaction mixture, followed by extraction with ethyl acetate (100 mL). The organic layer was washed sequentially with water and saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=80/20) to obtain 2-fluoro-6-(tetrahydro-2H-pyran-4-ylmethoxy)pyridine (1.36 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate (100 mL)
  2. washThe organic layer was washed sequentially with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=80/20)

Sources & evidence

ORD record
ord-cc0189e4389f4d329611f5242dc76ba5
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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