Sodium Sulfate → HCID 58181151, compound

HRID 469368Notes

Reaction equation

HRID 469368 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH3:17])[C:10]([CH3:19])([CH3:18])[C:9]1=O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[CH3:17])[C:10]([CH3:19])([CH3:18])[CH2:9]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 130305951,3,3,7-Tetramethylindolin-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 58181151HCID 58181151, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Under an argon atmosphere 5.71 mL of a 1 molar lithium aluminium hydride solution in THF were added dropwise to 600 mg (2.85 mmol) 1,3,3,7-tetramethyl-1,3-dihydro-indol-2-one in 20 mL THF. The reaction mixture was stirred for 2.5 h at 60° C. and then cooled to RT. While cooling with the ice bath, saturated, aqueous sodium sulphate solution was slowly added dropwise and the resulting suspension was filtered through Celite. The filtrate was combined with EtOAc and saturated sodium chloride solution. The organic phase was dried on sodium sulphate, filtered and the filtrate was evaporated down.

Workup

  1. temperaturecooled to RT
  2. filtrationthe resulting suspension was filtered through Celite
  3. customThe organic phase was dried on sodium sulphate
  4. filtrationfiltered
  5. customthe filtrate was evaporated down

Sources & evidence

ORD record
ord-9ae7a67680634975a0df844474a652a2
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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