Methyl iodide → Ethyl 6-methoxybenzo[D]isoxazole-3-carboxylate

HRID 424638

Reaction equation

HRID 424638 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].IC.[OH:9][C:10]1[CH:23]=[CH:22][C:13]2[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:15][O:16][C:12]=2[CH:11]=1>CN(C)C=O.O>[CH3:1][O:9][C:10]1[CH:23]=[CH:22][C:13]2[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:15][O:16][C:12]=2[CH:11]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 136216618Ethyl 6-hydroxybenzo[d]isoxazole-3-carboxylate

Product 1

HCID 53249635Ethyl 6-methoxybenzo[D]isoxazole-3-carboxylateYield 19%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (9.42 mmol) and iodomethane (8.45 mmol) were added to a solution of crude ethyl 6-hydroxybenzo[d]isoxazole-3-carboxylate (2.42 mmol) in N,N-dimethylformamide (30 mL) and the reaction mixture was maintained for 48 h at rt in the dark. The reaction mixture was diluted with water (100 mL) and was extracted with ethyl acetate (2×100 mL). The combined organic layers were washed with brine (3×100 mL), dried (magnesium sulfate), and concentrated. The residue was purified by chromatography (30/1 petroleum ether/ethyl acetate) to provide ethyl 6-methoxybenzo[d]isoxazole-3-carboxylate in 19% yield as a yellow solid.

Workup

  1. extractionwas extracted with ethyl acetate (2×100 mL)
  2. washThe combined organic layers were washed with brine (3×100 mL)
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (30/1 petroleum ether/ethyl acetate)

Sources & evidence

ORD record
ord-323718e9586a4c898858ef8e34938bb6
Source dataset
uspto-grants-2012_01
Patent number
US08106066B2

Linked notes

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