Aluminum(III) Chloride → HCID 15859200, compound

HRID 583192Notes

Reaction equation

HRID 583192 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[H-].[Al+3].[Li+].[H-].[H-].[H-].O[C:12]1([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2[CH:26]=[CH:25][C:24]3[O:27][CH2:28][O:29][C:23]=3[CH:22]=2)=[N:13]1>C1COCC1.CCOCC>[CH3:37][O:36][C:33]1[CH:34]=[CH:35][C:30]([CH:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]([C:21]3[CH:26]=[CH:25][C:24]4[O:27][CH2:28][O:29][C:23]=4[CH:22]=3)[NH:13]2)=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 18933561HCID 18933561, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15859200HCID 15859200, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a flask containing dry ether (2 ml) was added with stirring aluminum chloride (0.037 g, 0.28 nmmol) at 0° C. under argon, followed by 1M lithium aluminum hydride in THF (0.28 ml, 0.28 mmol). The mixture was stirred at 0° C. for 5 minutes, then to it was rapidly added (1RS)-1-Hydroxy-1-(4-methoxyphenyl)-3-(3,4-methylenedioxyphenyl)-1H-isoindole (0.050 g, 0.14 mmol), followed by dry THF (2 ml). After stirring for 10 minutes at 0° C. the reaction was quenched with water, 15% sodium hydroxide, and water. The mixture was extracted with ethyl acetate and the combined organic extract was successively washed with: water, brine and dried (MgSO4). After removing the solvent, flash chromatography of the residue (silica gel, 3:7 ethyl acetate:hexane) afforded the title compound as a yellow solid (0.030 g, 45%). MS (ESI) mle 346 [M+H]+ ; mp: 123-125° C.

Workup

  1. stirringAfter stirring for 10 minutes at 0° C. the reaction
  2. customwas quenched with water, 15% sodium hydroxide, and water
  3. extractionThe mixture was extracted with ethyl acetate
  4. extractionthe combined organic extract
  5. washwas successively washed with: water, brine
  6. dry with materialdried (MgSO4)
  7. customAfter removing the solvent, flash chromatography of the residue (silica gel, 3:7 ethyl acetate:hexane)

Sources & evidence

ORD record
ord-139cffec643e4cc1b3820e6d9c234d8b
Source dataset
uspto-grants-1999_07
Patent number
US05929106

Reaction notes

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