Acetic Acid → HCID 11789279, compound

HRID 278407Notes

Reaction equation

HRID 278407 reaction equation
OC1ON=[C:4]([CH3:7])[C:3]=1[C:8]1[O:12][N:11]=[C:10]([CH3:13])[CH:9]=1.C(O)(=[O:16])C.CO.Cl>[Fe].O>[CH2:3]([C:8]1[O:12][N:11]=[C:10]([CH3:13])[CH:9]=1)[C:4]([CH3:7])=[O:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 887MethanolHCID 178422859HCID 178422859, compound

Product 1

HCID 11789279HCID 11789279, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

9.70 g of 5-hydroxy-3-methyl-4-(3-methylisooxazol-5-yl)isoxazole was added to 18 ml of acetic acid and 30 ml of methanol, and was heated to 60° C. to dissolve. To the resulting solution was added 3.20 g of electrolytic iron powder to stir for an hour at 60° C. 20 ml of 3N hydrochloric acid was further added to the reaction solution to stir for 20 minutes at 60° C. The reaction mixture was cooled to room temperature and water was added. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated salt water, dried over anhydrous magnesium sulfate and concentrated to give 6.00 g of the title compound as a reddish brown liquid.

Workup

  1. dissolutionto dissolve
  2. stirringto stir for 20 minutes at 60° C
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated salt water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-39d0e7c5ad944146a38f0d09853d1265
Source dataset
uspto-grants-2002_03
Patent number
US06359143B1

Reaction notes

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