Aluminum(III) Chloride → HCID 178436241, compound

HRID 1814616Notes

Reaction equation

HRID 1814616 reaction equation
[C:1]([C:5]1[CH:9]=[CH:8][C-:7]([C:10](=O)[CH3:11])[C:6]=1[C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:4])([CH3:3])[CH3:2].[C:17]([C-:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1)(=O)[CH3:18].[Fe+2:25].[Al+3].[Cl-].[Cl-].[Cl-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC.CCCCCC>[C:1]([C:5]1[CH:9]=[CH:8][C-:7]([CH2:10][CH3:11])[C:6]=1[C:13]([CH3:14])([CH3:16])[CH3:15])([CH3:4])([CH3:3])[CH3:2].[CH2:17]([C-:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1)[CH3:18].[Fe+2:25]

Participants

6

Reactant 3

HCID 6451240Aluminum(III) Chloride2×HCID 21226445Aluminium lithium hydrideHCID 178466250HCID 178466250, compound2×

Product 1

HCID 178436241HCID 178436241, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

After the di-tert-butyl-diacetylferrocene was prepared, a Schlenk flask under positive nitrogen pressure was charged with 25 ml of dry Et2O. Second 0.35 g (2.61 mmol) of AlCl3 was charged into the reaction flask. Agitation was initiated and the AlCl3 dissolved into solution. Third, 5.23 ml (5.23 mmol) of 1M LiAlH4 in Et2O was charged into the reaction flask via syringe. The resulting suspension was agitated for approximately 15 minutes. Fourth, 1.00 g (2.62 mmol) of the above-prepared di-tert-butyl-diacetylferrocene was slowly charged into the reaction vessel. Next, the solution was heated to reflux for approximately 3 hours and then cooled to room temperature overnight with continuous agitation. The reaction was then quenched by the slow addition of Et2O to the solution. The organic layer was separated from the aqueous layer—via separatory funnel. Next, the aqueous layer was extracted with 100 ml of wet Et2O. The organic portions were combined and washed with H2O and brine, which was followed by drying over MgSO4. The solution was decanted from the drying agent and filtered. Next the solvent was stripped via rotary evaporation, which yielded a yellow-orange oil. The oil was dissolved in a small amount of hexane, applied to a vacuum assisted silica gel column, and eluted with more hexane. Upon solvent removal, 0.627 g of di-tert-butyl-diethylferrocene was collected and stored for later use.

Workup

  1. temperatureNext, the solution was heated
  2. temperatureto reflux for approximately 3 hours
  3. customThe reaction was then quenched by the slow addition of Et2O to the solution
  4. customThe organic layer was separated from the aqueous layer—via separatory funnel
  5. extractionNext, the aqueous layer was extracted with 100 ml of wet Et2O
  6. washwashed with H2O and brine, which
  7. dry with materialby drying over MgSO4
  8. customThe solution was decanted from the drying agent
  9. filtrationfiltered
  10. customNext the solvent was stripped via rotary evaporation, which
  11. customyielded a yellow-orange oil
  12. washeluted with more hexane
  13. customUpon solvent removal, 0.627 g of di-tert-butyl-diethylferrocene
  14. customwas collected

Sources & evidence

ORD record
ord-62a127b2bb2c4ec0b6eb0523ae00f844
Source dataset
uspto-grants-2005_04
Patent number
US06876478B2

Reaction notes

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