Water → N-methanesulfonyl-6-hydroxymethylindole

HRID 618268Notes

Reaction equation

HRID 618268 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][S:8]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20](OC)=[O:21])[CH:18]=2)[CH:13]=[CH:12]1)(=[O:10])=[O:9].O.[OH-].[Na+]>C1COCC1>[CH3:7][S:8]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][OH:21])[CH:18]=2)[CH:13]=[CH:12]1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 18789637n-Methanesufonyl-6-carbomethoxyindoleHCID 21226445Aluminium lithium hydride

Product 1

HCID 18789614N-methanesulfonyl-6-hydroxymethylindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminum hydride (1M) in THF (2.57 mmol, 2.57 ml) was added dropwise to a 0° C. solution of N-methanesufonyl-6-carbomethoxyindole in dry THF (10 mL, from above). After 30 min, 0.5 ml of water was added dropwise followed by the addition of 0.5 ml 1.0M NaOH solution. Celite was added and the mixture was filtered through a coarse fritted funnel. The solids were washed with 20 ml ethyl acetate. The filtrate was concentrated under vacuum. The product was purified by flash column chromatography (silica gel, applied to column with toluene, gradient elution 20-50% ethyl acetate/hexane) to give 370 mg of N-methanesulfonyl-6-hydroxymethylindole, a white solid (80% yield).

Workup

  1. additionCelite was added
  2. filtrationthe mixture was filtered through a coarse fritted funnel
  3. washThe solids were washed with 20 ml ethyl acetate
  4. concentrationThe filtrate was concentrated under vacuum
  5. customThe product was purified by flash column chromatography (silica gel, applied to column with toluene, gradient elution 20-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5d5d02e620da44fbbbc0fb10ed982890
Source dataset
uspto-grants-1999_09
Patent number
US05952362

Reaction notes

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