Toluene → 2-{4-(2-Octylindane-5-yl) phenyl}ethanol

HRID 1457495Notes

Reaction equation

HRID 1457495 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].Br[C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][OH:30])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[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(O)C>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][OH:30])=[CH:24][CH:23]=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 1140TolueneHCID 10340Sodium CarbonateHCID 728512-(4-Bromophenyl)ethanolHCID 220990862-Octylindane-5-boronic acid

Product 1

HCID 537769502-{4-(2-Octylindane-5-yl) phenyl}ethanolYield 68%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolvent

Procedure

2.74 g (10.0 mmol) of 2-octylindane-5-boronic acid, 2.0 g (10.0 mmol) of 2-(4-bromophenyl) ethanol, 0.38 g of tetrakis (triphenylphosphine) palladium, 15 ml of 2M-sodium carbonate solution, 15 ml of toluene and 10 ml of ethanol were heated at 80° C. for 6 hours under presence of nitrogen. After reactions had been completed, extraction with toluene was performed. Then, the extracted solution was dried with anhydrous sodium sulfate. The solvent was removed by filtration, and then refining was performed by re-crystallization (hexane/ethanol) so that 2.40 g of 2-{4-(2-octylindane-5-yl) phenyl}ethanol was obtained (yield 68%).

Workup

  1. extractionextraction with toluene
  2. dry with materialThen, the extracted solution was dried with anhydrous sodium sulfate
  3. customThe solvent was removed by filtration
  4. customrefining was performed by re-crystallization (hexane/ethanol) so that 2.40 g of 2-{4-(2-octylindane-5-yl) phenyl}ethanol
  5. customwas obtained (yield 68%)

Sources & evidence

ORD record
ord-773d46333c1f4e3aa54674019cc09a0f
Source dataset
uspto-grants-1998_12
Patent number
US05849217

Reaction notes

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