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Ethanol → 2-Octyl-5-[4-(4-decylphenyl)phenyl]indan

HRID 1770179
Notes
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Reaction equation

HRID 1770179 reaction equation
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14](B(O)O)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O([C:29]1[CH:34]=[CH:33][C:32]([C:35]2[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:37][CH:36]=2)=[CH:31][CH:30]=1)S(C(F)(F)F)(=O)=O.C(O)C.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.C1(C)C=CC=CC=1.O>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:29]3[CH:34]=[CH:33][C:32]([C:35]4[CH:36]=[CH:37][C:38]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50])=[CH:39][CH:40]=4)=[CH:31][CH:30]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 200950184-(4-Decylphenyl)phenyl triflateHCID 220990862-Octylindane-5-boronic acid

Product 1

HCID 200950092-Octyl-5-[4-(4-decylphenyl)phenyl]indanYield 41.3%

Reagents, catalysts & solvents 4

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 962WaterSolvent
HCID 1140TolueneSolvent2×
HCID 8857Ethyl AcetateSolvent

Procedure

0.55 g (2.01 mM of 2-octylindan-5-boronic acid, 0.80 g (1.81 mM) of 4-(4-decylphenyl)phenyl triflate, 1.5 ml of ethanol, 2.8 ml of toluene, 2.8 ml of 2M-sodium carbonate aqueous solution and 0.09 g of tetrakis(triphenylphosphine)palladium (O) were mixed and heat-refluxed for 4 hours under stirring. After the reaction, the reaction mixture, water and toluene were added to followed by filtration under reduced pressure. The toluene layer was washed with a common salt aqueous solution followed by drying with anhydrous sodium sulfate. Then, the sodium sulfate was removed from the mixture and the resultant mixture was evaporated to obtain a residue. Ethyl acetate was added to the residue and cooled with ice water to precipitate a crystal. The crystal was recovered by filtration and purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (toluene/ethyl acetate). The resultant crystal was further purified by silica gel column chromatography (eluent: toluene/hexane=2/1) and recrytallized from a mixture solvent (toluene/hexane) to obtain 0.39 g of 2-octyl-5-[4-(4-decylphenyl)phenyl]indan (Yield: 41.3%). ##STR312##

Workup

  1. temperatureheat-refluxed for 4 hours
  2. customAfter the reaction
  3. filtrationto followed by filtration under reduced pressure
  4. washThe toluene layer was washed with a common salt aqueous solution
  5. dry with materialby drying with anhydrous sodium sulfate
  6. customThen, the sodium sulfate was removed from the mixture
  7. customthe resultant mixture was evaporated
  8. customto obtain a residue
  9. customto precipitate a crystal
  10. filtrationThe crystal was recovered by filtration
  11. custompurified by silica gel column chromatography (eluent: toluene)
  12. customrecrystallized from a mixture solvent (toluene/ethyl acetate)
  13. customThe resultant crystal was further purified by silica gel column chromatography (eluent: toluene/hexane=2/1)

Sources & evidence

ORD record
ord-d73912c00e2b4be48e32228be6526208
Source dataset
uspto-grants-1995_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05385692

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes