Pyridine → HCID 23157559, compound

HRID 508002Notes

Reaction equation

HRID 508002 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:9].[OH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][CH2:14][C:15]2=[O:20].C(=O)([O-])[O-].[K+].[K+].N1C=CC=CC=1>[Cu]=O.CO.C1(C)C=CC=CC=1.CC1C=CC=CC=1C>[CH3:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[O:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][CH2:14][C:15]2=[O:20]

Participants

9

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 684712-Bromo-m-xyleneHCID 5905474-Hydroxy-1-indanone

Product 1

HCID 23157559HCID 23157559, compoundYield 2.2%

Reagents, catalysts & solvents 4

HCID 14829Copper oxideCatalystHCID 887MethanolSolventHCID 1140TolueneSolventHCID 7237O-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-bromo-1,3-dimethylbenzene (15.0 g, 81.1 mmol), 4-hydroxyindan-1-one (10.0 g, 67.5 mmol), copper(II) oxide (9.13 g, 114 mmol), potassium carbonate (18.7 g, 135 mmol), pyridine (200 mL) and o-xylene (100 mL) was stirred under a nitrogen atmosphere at 130° C. for 18 hr. After cooling the reaction mixture, a mixed solvent of toluene and methanol was added. The insoluble material was filtered off, and the filtrate was concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with 1 M hydrochloric acid, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Chloroform was added to the residue, the insoluble material was filtered off and the filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=90/10-hexane/ethyl acetate=0/100) to give the title compound (0.373 g, yield 2%) as a yellow oil.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationThe insoluble material was filtered off
  3. concentrationthe filtrate was concentrated
  4. additionWater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with 1 M hydrochloric acid, water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionChloroform was added to the residue
  10. filtrationthe insoluble material was filtered off
  11. customthe filtrate was purified by silica gel column chromatography (hexane/ethyl acetate=90/10-hexane/ethyl acetate=0/100)

Sources & evidence

ORD record
ord-0934ad22e5e04abaa2d0fed6d89c4929
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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