Water → HCID 57517501, compound

HRID 2368112Notes

Reaction equation

HRID 2368112 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:19][O:20][CH2:21]Cl.O>CN(C=O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([O:12][CH2:19][O:20][CH3:21])=[CH:10][N:11]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 575175006-(Cyclopropylmethoxy)pyridin-3-ol

Product 1

HCID 57517501HCID 57517501, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 6-(cyclopropylmethoxy)pyridin-3-ol (855 mg) and potassium carbonate (1.44 g) in DMF (15 mL) was added chloromethyl methyl ether (0.635 mL), and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed twice with saturated brine, and 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) to give the title compound (789 mg) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed twice with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-178024f53c8f4668a67b71c478aac02d
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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