Ethanol → HCID 178442568, compound

HRID 1770177Notes

Reaction equation

HRID 1770177 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].[CH2:21]([C@H:26]1[CH2:31][CH2:30][C@H:29]([C:32]2[CH:37]=[CH:36][C:35](Br)=[CH:34][CH:33]=2)[CH2:28][CH2:27]1)[CH2:22][CH2:23][CH2:24][CH3:25].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.C1C=CC=CC=1>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:35]3[CH:34]=[CH:33][C:32]([C@H:29]4[CH2:30][CH2:31][C@H:26]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:27][CH2:28]4)=[CH:37][CH:36]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 220990862-Octylindane-5-boronic acidHCID 178444243HCID 178444243, compound

Product 1

HCID 178442568HCID 178442568, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 241BenzeneSolvent

Procedure

1.78 g (6.5 mM) of 2-octylindan-5-boronic acid, 2.0 g (6.5 mM) of 4-(trans-4-pentylcyclohexy)phenyl bromide, 4 ml of ethanol, 8 ml of benzene, 8 ml of 2M-sodium carbonate aqueous solution and 0.24 g of tetrakis (triphenylphosphine) palladium (O) were mixed and heat-refluxed for 5 hours under stirring. After the reaction, the reaction mixture was poured into ice water, followed by extraction with toluene, washing with water and drying with anhydrous sodium sulfate. Then, the sodium sulfate was removed from the mixture and the resultant mixture was evaporated to obtain a residue. The residue was purified by silica gel column chromatography (eluent: hexane) and recrystallized from a mixture solvent (toluene/methanol) to obtain 1.52 g of 2-octyl-5-[4-(trans-4-pentylcyclohexyl)phenyl]indan (Yield: 51.0%). ##STR310##

Workup

  1. temperatureheat-refluxed for 5 hours
  2. customAfter the reaction
  3. extractionfollowed by extraction with toluene
  4. washwashing with water
  5. dry with materialdrying 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. customThe residue was purified by silica gel column chromatography (eluent: hexane)
  10. customrecrystallized from a mixture solvent (toluene/methanol)

Sources & evidence

ORD record
ord-7a009d87c54740418c3775e8eb6d4111
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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