Potassium Carbonate → Methyl [(5-nitro-1,2-benzisoxazol-3-yl)oxy]acetate

HRID 369593Notes

Reaction equation

HRID 369593 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][N:10]=[C:9]([OH:12])[C:8]=2[CH:13]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]([O:24][CH3:25])=[O:23]>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][N:10]=[C:9]([O:12][CH2:21][C:22]([O:24][CH3:25])=[O:23])[C:8]=2[CH:13]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178526505HCID 178526505, compound

Product 1

HCID 53638345Methyl [(5-nitro-1,2-benzisoxazol-3-yl)oxy]acetateYield 50.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-nitro-1,2-benzisoxazol-3-ol (3.90 g, 0.0220 mol) and potassium carbonate (4.17 g, 0.0300 mol) in N,N-dimethylformamide is stirred for 30 minutes, treated with methyl bromoacetate (3.96 g, 0.0260 mol), stirred overnight at room temperature, and poured into an acidic ice-water mixture. The resultant aqueous mixture is extracted with ethyl acetate. The organic extracts are combined, washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain a yellow oil. Column chromatography of the oil using silica gel and a (1:1) to (4:1) methylene chloride/hexanes gradient gives the title product as a white solid (2.80 g, mp 72-73.5° C.) which is identified by NMR spectral analyses.

Workup

  1. stirringstirred overnight at room temperature
  2. extractionThe resultant aqueous mixture is extracted with ethyl acetate
  3. washwashed sequentially with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a yellow oil

Sources & evidence

ORD record
ord-c0aebb8c3bd4450a87a9a78dfcfbf024
Source dataset
uspto-grants-2000_10
Patent number
US06140270

Reaction notes

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