Sodium Sulfate → 2-Benzyl-4-hydroxymethylisoindoline

HRID 1494846Notes

Reaction equation

HRID 1494846 reaction equation
[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[C:17](OC)=[O:18])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[CH2:17][OH:18])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 19828480Methyl 2-benzylisoindoline-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 198285052-Benzyl-4-hydroxymethylisoindolineYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

8.02 g of 2-benzyl-4-methoxycarbonylisoindoline was dissolved in 20 ml of anhydrous tetrahydrofuran and to the solution was added 1.9 g of lithium aluminum hydride. After stirring for 20 hours at room temperature, an aqueous solution of sodium sulfate was added. Insoluble materials were removed by filtration, the filtrate was concentrated, and the residue was recrystallized from ether to give 5.27 g of 2-benzyl-4-hydroxymethylisoindoline.

Workup

  1. customInsoluble materials were removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customthe residue was recrystallized from ether

Sources & evidence

ORD record
ord-d3612332c92c44609cd395b0ff479db7
Source dataset
uspto-grants-1991_06
Patent number
US05026856

Reaction notes

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