Hydrochloric Acid → Methyl 2-[(6-chloro-1,2-benzisoxazol-3-yl)oxy]propionate

HRID 375065Notes

Reaction equation

HRID 375065 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([OH:9])=[N:7][O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21].Cl>CN(C)C=O.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([O:9][CH:19]([CH3:24])[C:20]([O:22][CH3:23])=[O:21])=[N:7][O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 95576Methyl 2-bromopropionateHCID 178518989HCID 178518989, compound

Product 1

HCID 22402920Methyl 2-[(6-chloro-1,2-benzisoxazol-3-yl)oxy]propionate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-chloro-1,2-benzisoxazol-3-ol (6.8 g, 40.1 mmol), potassium carbonate (8.3 g, 60 mmol) and methyl 2-bromopropionate (10.0 g, 60.1 mmol) in N,N-dimethylformamide is stirred at room temperature overnight and diluted with water. The resultant aqueous mixture is acidified with concentrated hydrochloric acid (pH5-pH6) and extracted with methylene chloride. The combined organic extracts are diluted with hexanes, washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Column chromatography of the residue using silica gel and ethyl acetate/hexanes solutions gives the title product as a gold oil which is identified by NMR spectral analyses.

Workup

  1. extractionextracted with methylene chloride
  2. additionThe combined organic extracts are diluted with hexanes
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto obtain a residue

Sources & evidence

ORD record
ord-966e3a350c72442cb01ffc6440e9eb53
Source dataset
uspto-grants-1996_01
Patent number
US05484763

Reaction notes

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