Water → HCID 58047409, compound

HRID 1888708Notes

Reaction equation

HRID 1888708 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]2[C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[N:8][O:9][C:5]=2[CH:4]=1.[H-].[Na+].[CH3:19]I.O>C1COCC1>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]2[C:7]([CH:10]([CH3:19])[C:11]([O:13][CH3:14])=[O:12])=[N:8][O:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57349049Methyl (6-methoxy-1,2-benzoxazol-3-yl)acetate

Product 1

HCID 58047409HCID 58047409, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl (6-methoxy-1,2-benzisoxazol-3-yl)acetate (3.00 g, 13.6 mmol) in anhydrous THF (70 mL) was added 60% sodium hydride (544 mg, 13.6 mmol) under ice-cooling. After stirring for 30 min, methyl iodide (0.929 mL, 14.9 mmol) in THF (4 mL) was added dropwise thereto, and the mixture was stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with 10% aqueous potassium carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. This solution was applied to basic silica gel column chromatography (ethyl acetate) to give the title compound (3.19 g, quantitative) as an oil.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with 10% aqueous potassium carbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-68165045066e400099eb76dbd9908e0d
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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