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Aluminum(III) Chloride → 1-Benzyloxy-2-(4-fluorophenyl)-4-ethyl-5-[(4-aminobutyl)oxy]-benzene

HRID 1835596
Notes
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Reaction equation

HRID 1835596 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:11]([O:18][C:19]1[CH:24]=[C:23]([O:25][CH2:26][CH2:27][CH2:28][C:29]#[N:30])[C:22]([CH2:31][CH3:32])=[CH:21][C:20]=1[C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCOCC>[CH2:11]([O:18][C:19]1[CH:24]=[C:23]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][NH2:30])[C:22]([CH2:31][CH3:32])=[CH:21][C:20]=1[C:33]1[CH:34]=[CH:35][C:36]([F:39])=[CH:37][CH:38]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 235018421-Benzyloxy-2-(4-fluorophenyl)-4-ethyl-5-[(3-cyanopropyl)oxy]-benzene

Product 1

HCID 235017961-Benzyloxy-2-(4-fluorophenyl)-4-ethyl-5-[(4-aminobutyl)oxy]-benzeneYield 47.1%

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent
2×

Procedure

Dry ether (10 mL) was added to anhydrous aluminum chloride (693 mg) at 0° C. under nitrogen and stirred until dissolution was complete. Lithium aluminum hydride (197 mg) was added in one portion and the solution heated to reflux. 1-Benzyloxy-2-(4-fluorophenyl)-4-ethyl-5-[(3-cyanopropyl)oxy]-benzene (1.05 g) dissolved in dry ether (5 mL) was added dropwise at reflux. The heat was removed and the mixture stirred at ambient temperature for 4.5 hours. The reaction was quenched by addition of water, followed by 6N sulfuric acid until a clear solution was obtained. This was extracted with ether. The aqueous solution was cooled and treated with 50% sodium hydroxide. The basic mixture was extracted with ether. The organic layers were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to afford 500 mg of 1-Benzyloxy-2-(4-fluorophenyl)-4-ethyl-5-[(4-aminobutyl)oxy]-benzene as an oil, which was not further purified but carried forward. Mass Spec (EI), m/e=394.3 (M+H)

Workup

  1. temperaturethe solution heated to reflux
  2. additionwas added dropwise
  3. temperatureat reflux
  4. customThe heat was removed
  5. stirringthe mixture stirred at ambient temperature for 4.5 hours
  6. customThe reaction was quenched by addition of water
  7. customwas obtained
  8. extractionThis was extracted with ether
  9. temperatureThe aqueous solution was cooled
  10. additiontreated with 50% sodium hydroxide
  11. extractionThe basic mixture was extracted with ether
  12. dry with materialThe organic layers were dried over magnesium sulfate
  13. filtrationfiltered
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c3170b68e9d342999406700553de7565
Source dataset
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06770259B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes