Sodium sulfate decahydrate → HCID 57901683, compound

HRID 1851410Notes

Reaction equation

HRID 1851410 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[C:15](OCC1C=CC=CC=1)=[O:16].[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.C(OCC)(=O)C>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:15][OH:16]

Participants

6

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydride2×HCID 57901835HCID 57901835, compound

Product 1

HCID 57901683HCID 57901683, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 2-(1,3-thiazol-2-yl)-1H-indole-7-carboxylate (1.39 g) in tetrahydrofuran (30 mL) was added lithium aluminum hydride (0.200 g), and the mixture was stirred at room temperature for 1 hr. Lithium aluminum hydride (0.600 g) was added to the reaction solution, and the mixture was stirred at room temperature for 4 hr. Sodium sulfate-decahydrate (7.80 g) was added to the reaction mixture, and the mixture was stirred for 30 min and diluted with ethyl acetate. The obtained suspension was filtered through celite, washed with ethyl acetate, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=15:85-70:30) to give the title compound (0.564 g, yield 59%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 4 hr
  2. stirringthe mixture was stirred for 30 min
  3. filtrationThe obtained suspension was filtered through celite
  4. washwashed with ethyl acetate
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=15:85-70:30)

Sources & evidence

ORD record
ord-3b379d25f0d9443fb01c15e2dfd7cca0
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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