Methanol → HCID 23157183, compound

HRID 507976Notes

Reaction equation

HRID 507976 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].CO>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.O>[CH3:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=1[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2

Participants

9

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 5206955-Bromo-1-indanoneHCID 5833222,6-Dimethylphenylboronic acid

Product 1

HCID 23157183HCID 23157183, compoundYield 54.3%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-bromoindan-1-one (1.20 g, 5.69 mmol), 2,6-dimethylphenylboronic acid (1.02 g, 6.82 mmol), tetrakis(triphenylphosphine)palladium(0) (328 mg, 0.285 mmol), sodium carbonate (1.81 g, 17.1 mmol), methanol (8 mL), water (8 mL) and toluene (25 mL) was heated under reflux overnight under an argon atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate, washed with water, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-50% ethyl acetate/hexane) to give the title compound (0.73 g, yield 54%) as a colorless oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight under an argon atmosphere
  3. temperatureAfter cooling
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (5%-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3c5bcd73e1304f3ea4777a7944246c99
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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