Methanol → HCID 90384337, compound

HRID 928667Notes

Reaction equation

HRID 928667 reaction equation
[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH2:11]Br)[C:6]=2[C:5]([F:13])=[C:4]([F:14])[CH:3]=1.C([O-])(=[O:17])C.[K+].CO.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[C:10]2[O:9][CH:8]=[C:7]([CH2:11][OH:17])[C:6]=2[C:5]([F:13])=[C:4]([F:14])[CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 517044Potassium AcetateHCID 90384261HCID 90384261, compound

Product 1

HCID 90384337HCID 90384337, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

The compound (1.47 g, 4.51 mmol) obtained in Step 1 was dissolved in acetonitrile (50 mL), and potassium acetate (660 mg, 6.76 mmol) was added thereto, and stirred at 60° C. for 3 hours. After cooling, the solvent was distilled away, and to the resulting residue, methanol (20 mL) and potassium carbonate (1.56 g, 11.28 mmol) were added, and stirred at room temperature for 2 hours. The solvent was distilled away. After diluted with ethyl acetate, the resultant was washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was distilled away, and the resulting residue was purified by silica gel chromatography (hexane/ethyl acetate) to thus obtain the title compound.

Workup

  1. temperatureAfter cooling
  2. distillationthe solvent was distilled away
  3. stirringstirred at room temperature for 2 hours
  4. distillationThe solvent was distilled away
  5. additionAfter diluted with ethyl acetate
  6. washthe resultant was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled away
  9. customthe resulting residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f2ea8db8c8f7438ebee8958f00334b86
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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