Potassium Carbonate → HCID 67290476, compound

HRID 511820Notes

Reaction equation

HRID 511820 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([CH3:12])=[N:10][CH:11]=2)[CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:18].C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([CH2:12][OH:18])=[N:10][CH:11]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 58520617HCID 58520617, compound

Product 1

HCID 67290476HCID 67290476, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(cyclopropylmethoxy)-2-methylpyridine (3.9 g, 24 mmol) in dichloromethane (50 mL) was added 3-chlorobenzoperoxoic acid (7.6 g, 32 mmol) at room temperature. After being stirred at room temperature for 1 hour, the mixture was poured into saturated aqueous sodium bicarbonate solution. The organic phase was extracted with dichloromethane (twice). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was dissolved in acetic anhydride (50 mL) and the mixture was stirred at 100° C. for 2 hours. Half of the solvent was removed under the reduced pressure. The residue was dissolved into methanol (50 mL). Potassium carbonate (20 g, 143 mmol) was added to the mixture carefully. The mixture was stirred at room temperature for 1 hour. The mixture was poured into H2O, and the aqueous phase was extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1 (v/v)) to give 4.5 g (quantitative yield) of the title compound as a brown oil:

Workup

  1. extractionThe organic phase was extracted with dichloromethane (twice)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in acetic anhydride (50 mL)
  5. stirringthe mixture was stirred at 100° C. for 2 hours
  6. customHalf of the solvent was removed under the reduced pressure
  7. dissolutionThe residue was dissolved into methanol (50 mL)
  8. stirringThe mixture was stirred at room temperature for 1 hour
  9. extractionthe aqueous phase was extracted with ethyl acetate (twice)
  10. dry with materialThe combined organic layers were dried over magnesium sulfate
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (1:1 (v/v))

Sources & evidence

ORD record
ord-efc7265f19e94df081b0cf761a0bdbe5
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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