Aluminium lithium hydride → HCID 21964288, compound

HRID 2212144Notes

Reaction equation

HRID 2212144 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:39]=[CH:38][C:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]4[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=4)=[CH:19][CH:20]=3)[CH:15]=[C:14]2[C:33](OCC)=[O:34])=[CH:10][CH:9]=1>C(OCC)C>[CH3:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][N:13]2[C:21]3[C:16](=[CH:17][C:18]([C:22]4[CH:27]=[CH:26][C:25]([O:28][C:29]([F:31])([F:32])[F:30])=[CH:24][CH:23]=4)=[CH:19][CH:20]=3)[CH:15]=[C:14]2[CH2:33][OH:34])=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21964300HCID 21964300, compound

Product 1

HCID 21964288HCID 21964288, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Lithium aluminum hydride (0.244 g, 6.1 mmol) was added portionwise to a stirring solution of ethyl 1-(4-methylbenzyl)-5-[4-(trifluoromethoxy)phenyl]-1H-indole-2-Carboxylate (2.0 g, 4.4 mmol) in ethyl ether (17 mL) at 0° C. under a nitrogen atmosphere over a period of 5 minutes. The mixture was then warmed up to room temperature. After the reaction mixture was stirred at room temperature for 5 hours, the reaction was carefully quenched with water and filtered. The filtrate was extracted with ethyl acetate. The organic extract was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated to afford the title compound as a white solid (1.56 g, 86%). Mass spectrum (ESI, [M+H]+) m/z 412.

Workup

  1. customthe reaction was carefully quenched with water
  2. filtrationfiltered
  3. extractionThe filtrate was extracted with ethyl acetate
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-6472525fd9ff474493ab6ed22d2a7957
Source dataset
uspto-grants-2006_09
Patent number
US07101903B2

Reaction notes

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