Potassium Carbonate → HCID 19802539, compound

HRID 1515107Notes

Reaction equation

HRID 1515107 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].B([O-])O[CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Ag]=O>[CH2:14]([C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11])[CH3:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 987131-Indanone, 4-bromo-HCID 178465749HCID 178465749, compound

Product 1

HCID 19802539HCID 19802539, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromoindan-1-one (600 mg, 2.84 mmol) was dissolved in toluene (10 mL), and ethyl boronate (105 mg, 8.52 mmol), silver oxide (I) (274 mg, 7.10 mmol), potassium carbonate (196 mg, 8.52 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloride dichloromethane complex (46 mg, 0.0568 mmol) were added thereto, and then, the resulting mixture was stirred under a nitrogen atmosphere at 100° C. for 4 hours. After cooling to room temperature, the reaction solution was filtered, and the solvent was distilled off under reduced pressure, whereby a crude product was obtained. This crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 80:20 (v/v)), whereby the objective title compound was obtained as a colorless oily substance (421 mg, yield: 92%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction solution was filtered
  3. distillationthe solvent was distilled off under reduced pressure, whereby a crude product
  4. customwas obtained
  5. customThis crude product was purified by silica gel column chromatography (hexane:ethyl acetate=100:0 to 80:20 (v/v)), whereby the objective title compound
  6. customwas obtained as a colorless oily substance (421 mg, yield: 92%)

Sources & evidence

ORD record
ord-3711b4d8779941d7be0f24dd2d05b756
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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