Water → HCID 135794325, compound

HRID 460592Notes

Reaction equation

HRID 460592 reaction equation
C[O:2][C:3]1[C:11]2[CH:10]=[C:9]([C:12](=O)[CH2:13][C:14](=O)[CH3:15])[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH3:18][NH:19][NH2:20].O>CO>[OH:2][C:3]1[C:11]2[CH:10]=[C:9]([C:12]3[CH:13]=[C:14]([CH3:15])[N:19]([CH3:18])[N:20]=3)[O:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6061MethylhydrazineHCID 227289761-(4-Methoxy-2-benzofuranyl)-1,3-butanedione

Product 1

HCID 135794325HCID 135794325, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-40 °C

Procedure

1-(4-Methoxybenzo(b)furan-2-yl)butan-1,3-dione (1.0 g) was dissolved in methanol (30 ml) and methylhydrazine (0.3 g) was added thereto. The mixture was refluxed under heating for 20 min. The reaction solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/acetone). To the obtained oil was added methylene chloride (30 ml), and the mixture was cooled to −40° C., and boron tribromide (1 ml) was added dropwise. After the completion of the reaction, the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and after filtration, the solvent was evaporated under reduced pressure to give 3-(4-hydroxybenzo(b)furan-2-yl)-1,5-dimethylpyrazole (0.85 g) as a brown oil. Using this and (S)-glycidyl nosylate (0.75 g) and in the same manner as in Starting Material Synthesis Example 1, the title compound (0.53 g) was obtained as a brown oil.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 20 min
  3. customThe reaction solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/acetone)
  5. additionTo the obtained oil was added methylene chloride (30 ml)
  6. additionboron tribromide (1 ml) was added dropwise
  7. customAfter the completion of the reaction
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. filtrationafter filtration
  11. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f21139ea4be74816bac144a55872fa99
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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