Aluminum isopropoxide → HCID 68285922, compound

HRID 534681Notes

Reaction equation

HRID 534681 reaction equation
CC(C)[O-].[Al+3].CC(C)[O-].CC(C)[O-].[CH3:14][O:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20](=O)[CH2:21][CH2:22][CH:23]2[CH2:26][C:27]#[N:28])=[CH:18][CH:17]=1>C(O)(C)C>[CH3:14][O:15][C:16]1[CH:25]=[C:24]2[C:19]([CH:20]=[CH:21][CH2:22][CH:23]2[CH2:26][C:27]#[N:28])=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 11143Aluminum isopropoxideHCID 68285998HCID 68285998, compound

Product 1

HCID 68285922HCID 68285922, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Aluminium isopropoxide (2.05 g, 10.0 mmol) is added to a solution of the compound obtained in Step B (680 mg, 3.15 mmol) in isopropanol (15 mL) at ambient temperature. The reaction mixture is refluxed. When the reagents have been completely consumed, a few crystals of p-toluenesulphonic acid monohydrate are added and a Dean-Stark apparatus is mounted on top of the flask. The mixture is again refluxed for 1 hour, during which the isopropanol is gradually replaced with toluene by means of the Dean-Stark apparatus. A 1N HCl solution is then added and the resulting phases are separated. The aqueous phase is extracted with ethyl acetate, the organic phases being washed with saturated NaHCO3 solution and with saturated NaCl solution, then dried over MgSO4, filtered and concentrated under reduced pressure. The residue is purified by column chromatography (petroleum ether-ethyl acetate: 80-20) to yield the title product in the form of an oil in a yield of 85%.

Workup

  1. temperatureThe reaction mixture is refluxed
  2. customWhen the reagents have been completely consumed
  3. additiona few crystals of p-toluenesulphonic acid monohydrate are added
  4. temperatureThe mixture is again refluxed for 1 hour, during which the isopropanol
  5. additionA 1N HCl solution is then added
  6. customthe resulting phases are separated
  7. extractionThe aqueous phase is extracted with ethyl acetate
  8. washthe organic phases being washed with saturated NaHCO3 solution and with saturated NaCl solution
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe residue is purified by column chromatography (petroleum ether-ethyl acetate: 80-20)

Sources & evidence

ORD record
ord-a62f435d25514885b0c2bbf9876c0d05
Source dataset
uspto-grants-2014_10
Patent number
US08853449B2

Reaction notes

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