Potassium Carbonate → HCID 117992246, compound

HRID 531124Notes

Reaction equation

HRID 531124 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[C:16]([Br:28])=[CH:17][C:18]2[C:23](=[O:24])[O:22][C:21]([CH3:26])(C)[O:20][C:19]=2[CH:27]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CO>[CH2:7]([O:14][C:15]1[C:16]([Br:28])=[CH:17][C:18]([C:23]([O:22][CH3:1])=[O:24])=[C:19]([O:20][CH2:21][CH3:26])[CH:27]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 117992149HCID 117992149, compound

Product 1

HCID 117992246HCID 117992246, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (7.57 g) was added to a mixture of 7-(benzyloxy)-6-bromo-2,2-dimethyl-4H-1,3-benzodioxin-4-one (9.95 g) and methanol (50 mL), and the resultant mixture was stirred overnight at room temperature. The reaction mixture was filtered through celite, and then, the solvent was distilled off under reduced pressure. Iodoethane (3.29 mL) was added to a DMF (50 mL) suspension of the obtained residue and potassium carbonate (7.57 g), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was allowed to cool to room temperature, and then, water was added thereto, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (9.80 g).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionIodoethane (3.29 mL) was added to a DMF (50 mL) suspension of the obtained residue and potassium carbonate (7.57 g)
  4. temperatureto cool to room temperature
  5. additionwater was added
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe obtained organic layer was washed with saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ed4b09fb6a6847d7afcecfd862d68120
Source dataset
uspto-grants-2016_05
Patent number
US09353108B2

Reaction notes

Loading…