Potassium Phosphate, Tribasic → HCID 67058094, compound

HRID 1515117Notes

Reaction equation

HRID 1515117 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-])O[CH:14]1[CH2:16][CH2:15]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH2:14]1[CH:16]([C:2]2[C:3]3[CH2:4][CH2:5][C:6](=[O:11])[C:7]=3[CH:8]=[CH:9][CH:10]=2)[CH2:15]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 987131-Indanone, 4-bromo-HCID 86647340HCID 86647340, compound

Product 1

HCID 67058094HCID 67058094, compoundYield 86.3%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

To a toluene (6.0 mL) solution of 4-bromoindan-1-one (300 mg, 1.42 mmol), water (0.30 mL), cyclopropyl borate (158 mg, 1.85 mmol), potassium phosphate (1.05 g, 4.97 mmol), tricyclohexylphosphine (a 0.48 M toluene solution, 0.295 mL, 0.142 mmol), and palladium acetate (16 mg, 0.071 mmol) were sequentially added, and the resulting mixture was stirred under a nitrogen atmosphere at 100° C. for 4 hours. After the reaction solution was cooled to room temperature, water was added thereto, and the organic matter was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, then dried over anhydrous sodium sulfate and filtered. Then, 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 light yellow solid (211 mg, yield: 86%).

Workup

  1. temperatureAfter the reaction solution was cooled to room temperature
  2. extractionthe organic matter was extracted with ethyl acetate
  3. washThe organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. distillationThen, the solvent was distilled off under reduced pressure, whereby a crude product
  7. customwas obtained
  8. 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

Sources & evidence

ORD record
ord-35974f84be0f4a6fba929ac20ea3f6ca
Source dataset
uspto-grants-2012_07
Patent number
US08222281B2

Reaction notes

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