Sodium sulfate decahydrate → HCID 68664421, compound

HRID 452721Notes

Reaction equation

HRID 452721 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:24]=[CH:23][C:18]([C:19](OC)=[O:20])=[CH:17][CH:16]=4)[C:11]=3[CH:25]=2)=[N:4][N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[O:14][CH:13]=[C:12]([C:15]4[CH:24]=[CH:23][C:18]([CH2:19][OH:20])=[CH:17][CH:16]=4)[C:11]=3[CH:25]=2)=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 44481209HCID 44481209, compound

Product 1

HCID 68664421HCID 68664421, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-[5-(5-methyl-1,3,4-oxadiazol-2-yl)-1-benzofuran-3-yl]benzoate (408 mg, 1.22 mmol) in tetrahydrofuran (35 mL) was added lithium aluminum hydride (46.3 mg, 1.22 mmol) at room temperature, and the resulting mixture was stirred for 10 min. Sodium sulfate decahydrate (393 mg, 1.22 mmol) was added to the reaction mixture, and the mixture was further stirred at room temperature for 1 hr. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (tetrahydrofuran) and recrystallized from hexane/tetrahydrofuran to give the title compound (321 mg, yield 86%) as colorless crystals.

Workup

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. customInsoluble material was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by basic silica gel column chromatography (tetrahydrofuran)
  5. customrecrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-fcc48b6b98464b27958d4d92c6e0dca3
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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