Hydrochloric Acid → HCID 86731313, compound

HRID 2277240Notes

Reaction equation

HRID 2277240 reaction equation
[F:1][C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][N:5]=[C:4]([CH:12]=[O:13])[CH:3]=1.P([O-])(O)(O)=O.[Na+].CC(=CC)C.Cl([O-])=O.[Na+].Cl.[C:30]([OH:34])(C)(C)C>O>[F:1][C:2]1[C:7]([O:8][CH2:9][O:10][CH3:11])=[CH:6][N:5]=[C:4]([C:12]([O:34][CH3:30])=[O:13])[CH:3]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6386tert-ButanolHCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86731312HCID 86731312, compound

Product 1

HCID 86731313HCID 86731313, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-fluoro-5-(methoxymethoxy)pyridine-2-carbaldehyde (2.43 g), sodium dihydrogen phosphate (4.72 g), 2-methyl-2-butene (7.32 mL), water (4 mL) and tert-butanol (20 mL) was added sodium chlorite (2.23 g), and the mixture was stirred at room temperature for 2.5 hr. The reaction mixture was acidified with 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in DMF (30 mL), potassium carbonate (1.81 g) and methyl iodide (0.820 mL) were added thereto, and the mixture was stirred at 70° C. for 20 min. To the reaction mixture was added water, and the obtained mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (1.80 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in DMF (30 mL)
  6. additionpotassium carbonate (1.81 g) and methyl iodide (0.820 mL) were added
  7. stirringthe mixture was stirred at 70° C. for 20 min
  8. additionTo the reaction mixture was added water
  9. extractionthe obtained mixture was extracted with ethyl acetate
  10. washThe extract was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c8ca71e40a7b446a84bf469b5e9fe2bc
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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