Methyl indole-6-carboxylate → 6-Hydroxymethylindole

HRID 1198555Notes

Reaction equation

HRID 1198555 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16](OC)=[O:17])[CH:14]=2)[CH:9]=[CH:8]1>C1COCC1>[OH:17][CH2:16][C:13]1[CH:14]=[C:15]2[C:10]([CH:9]=[CH:8][NH:7]2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 639844Methyl indole-6-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 27734596-Hydroxymethylindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminium hydride (6.18 g, 2 mol. eq.) in dry THF (350 ml) under nitrogen was added dropwise a solution of methyl indole-6-carboxylate (14.2 g, 81.1 mmol) in dry THF (350 ml) and stirred for 4 hours. The gelatinous suspension was quenched with 2N hydrochloric acid, extracted into diethyl ether, and the combined organic extracts dried, filtered and evaporated in vacuo to yield a yellow oil.

Workup

  1. customThe gelatinous suspension was quenched with 2N hydrochloric acid
  2. extractionextracted into diethyl ether
  3. customthe combined organic extracts dried
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto yield a yellow oil

Sources & evidence

ORD record
ord-a75853183b364191bf55dc1c83e4cfc6
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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