Aluminium lithium hydride → (2-(Methylsulfonyl)isoindolin-4-yl)methanol

HRID 1055406Notes

Reaction equation

HRID 1055406 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][S:8]([N:11]1[CH2:19][C:18]2[C:17]([C:20](OC)=[O:21])=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:12]1)(=[O:10])=[O:9]>C1COCC1.[OH-].[Na+]>[CH3:7][S:8]([N:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:20][OH:21])[CH2:12]1)(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90037438Methyl 2-(methylsulfonyl)isoindoline-4-carboxylate

Product 1

HCID 90036971(2-(Methylsulfonyl)isoindolin-4-yl)methanolYield 61%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

Lithium aluminum hydride (LAH, 1 M in THF, 2 mL, 2.0 mmol) was added to solution of methyl 2-(methylsulfonyl)isoindoline-4-carboxylate in THF (15 mL). After 10 h the mixture was diluted with 5% NaOH solution and extracted with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated. The residue was recrystallized from DCM to give the title compound (200 mg, 61%) as a grey solid.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was recrystallized from DCM

Sources & evidence

ORD record
ord-3d1642e670ea4cb6b0a027d4c3aac1d6
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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