Potassium Carbonate → HCID 86685010, compound

HRID 1518986Notes

Reaction equation

HRID 1518986 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(#N)C>[CH2:17]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127421-BromononaneHCID 754211H-indol-4-ol

Product 1

HCID 86685010HCID 86685010, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

4-Hydroxyindole (500 mg, 3.76 mmol), K2CO3 (1.04 g, 7.51 mmol), and n-nonylbromide (817 mg, 3.94 mmol) was dissolved in acetonitrile (10 mL) and stirred at 25° C. for 10 min in a 250 mL round bottom flask. The reaction mixture was refluxed for 24 h and cooled to 25° C. The reaction mixture filtered to remove insoluble impurities and solvent evaporated under reduced pressure. The residue was purified by flash chromatography eluting with 100% hexanes and 30% EtOAc/hexanes to afford 4-nonyloxyindole as pale yellow solid (847 mg, 87%). Rf=0.8 (30% EtOAc/hexanes).

Workup

  1. temperatureThe reaction mixture was refluxed for 24 h
  2. temperaturecooled to 25° C
  3. filtrationThe reaction mixture filtered
  4. customto remove insoluble impurities and solvent
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with 100% hexanes and 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-938b15c9ebe84d2c86b5e259d9cbc670
Source dataset
uspto-grants-2015_07
Patent number
US09073851B2

Reaction notes

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