Methyl iodide → HCID 69967351, compound

HRID 2289088Notes

Reaction equation

HRID 2289088 reaction equation
[OH:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:10]([CH2:11][CH2:12][CH3:13])[C:5]=2[O:4][N:3]=1.CI.[C:24](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:24][O:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([O:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:10]([CH2:11][CH2:12][CH3:13])[C:5]=2[O:4][N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178439644HCID 178439644, compound

Product 1

HCID 69967351HCID 69967351, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-hydroxy-6-benzyloxy-7-propylbenz-[4,5]-isoxazole (Step C; 195 mg) in acetone (3 mL) was treated with methyl iodide (0.067 mL) and potassium carbonate (100 mg). The mixture was refluxed for 8 hours. The reaction was partitioned between isopropyl acetate and pH 4 buffer. The organic was dried over magnesium sulfate, filtered and concentrated to a solid, which was chromatographed over silica gel to afford the title compound.

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. customThe reaction was partitioned between isopropyl acetate and pH 4 buffer
  3. dry with materialThe organic was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to a solid, which
  6. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-b698b95fbf314e46a399d2cb3c09cc88
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

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