Water → 4-(4-tert-butylphenyl)-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one

HRID 271792Notes

Reaction equation

HRID 271792 reaction equation
Br[C:2]1[C:13]2[CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]2[C:3]=1[CH2:4][CH:5]([CH3:15])[C:6]2=[O:14].C(OB([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)O)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+].O>C(COC)OC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:3]([C:23]1[CH:24]=[CH:25][C:26]([C:2]2[C:13]3[CH2:12][CH2:11][CH2:10][C:9]=3[CH:8]=[C:7]3[C:3]=2[CH2:4][CH:5]([CH3:15])[C:6]3=[O:14])=[CH:27][CH:28]=1)([CH3:7])([CH3:4])[CH3:2]

Participants

8

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 235470494-Bromo-2-methyl-2,3,6,7-tetrahydro-s-indacen-1(5H)-oneHCID 66584345Tert-butylphenylboronic acid

Product 1

HCID 687458344-(4-tert-butylphenyl)-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-oneYield 139.6%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

0.3 g of palladium acetate (3 mol %) and 0.7 g of triphenylphosphine (6 mol %) were added to a well-stirred mixture of 12 g (0.045 mol) of 4-bromo-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one (1b), 11.2 g (0.063 mol) of tert-butylphenylboronic acid and 13.4 g (0.126 mol) of sodium carbonate in 170 ml of dimethoxyethane (DME)/56 ml of water. The reaction mixture was refluxed for 6 hours, poured into water and extracted with methylene chloride (5×100 ml). The combined organic phases were washed with sodium carbonate solution and water and dried over magnesium sulfate. After removal of the solvent, the crude product was chromatographed on silica gel (hexane/chloroform from 4/1 to 1/1). This gave 10 g (70% yield) of the compound (1c) as a viscous oil.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours
  2. extractionextracted with methylene chloride (5×100 ml)
  3. washThe combined organic phases were washed with sodium carbonate solution and water
  4. dry with materialdried over magnesium sulfate
  5. customAfter removal of the solvent
  6. customthe crude product was chromatographed on silica gel (hexane/chloroform from 4/1 to 1/1)

Sources & evidence

ORD record
ord-6fb62cb35617479281ac8ec352db1097
Source dataset
uspto-grants-2008_11
Patent number
US07452949B2

Reaction notes

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