Hydrochloric Acid → 6-Hydroxymethylindole

HRID 864481Notes

Reaction equation

HRID 864481 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[CH:16][NH:17]2)=[CH:13][CH:12]=1)=O.O.Cl>[Na].O1CCCC1>[OH:8][CH2:9][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[CH:16][NH:17]2)=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 639844Methyl indole-6-carboxylateHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 27734596-Hydroxymethylindole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 5360545SodiumSolvent

Procedure

Lithium aluminium hydride (3.48 g, 91.70 mmol) was suspended in sodium-dried tetrahydrofuran (150 ml). The suspension was stirred under a nitrogen atmosphere. Methyl-(indol-6-yl)methanoate (8.0 g, 45.7 mmol) was dissolved in dry tetrahydrofuran (50 ml) and added dropwise to the lithium aluminium hydride suspension. The mixture was stirred at ambient temperature for three hours. Water (10 ml) was added dropwise, followed by 2N hydrogen chloride (30 ml). The mixture was extracted with diethyl ether (3×150 ml) to yield a light purple oil.

Workup

  1. stirringThe mixture was stirred at ambient temperature for three hours
  2. extractionThe mixture was extracted with diethyl ether (3×150 ml)
  3. customto yield a light purple oil

Sources & evidence

ORD record
ord-59a092bf5ca742a0a637c686b8d64f1d
Source dataset
uspto-grants-1996_10
Patent number
US05563147

Reaction notes

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