Tetrahydrofuran → 1H-indol-4-ylmethanol

HRID 2236432Notes

Reaction equation

HRID 2236432 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7](C(O)=O)[CH:8]=2)[CH:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:19]1CCC[CH2:20]1>>[NH:1]1[C:9]2[C:4](=[C:5]([CH2:20][OH:19])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 5952301H-indole-6-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 27734571H-indol-4-ylmethanol

Procedure

To a solution of 6-indole carboxylic acid (500 mg, 3.1 mmol) in tetrahydrofuran (31 ml) is added lithium aluminum hydride (590 mg, 15.5 mmol) at 0° C. The reaction mixture is refluxed for 6 hours. The resulting mixture is then quenched with 5% potassium hydrogen sulfate (20 ml) and extracted with ether (20 mL). The organic layer is then dried with sodium sulfate and concentrated to give a yellow solid (230 mg). MS (ESI) m/z 146.6 (M+1).

Workup

  1. temperatureThe reaction mixture is refluxed for 6 hours
  2. customThe resulting mixture is then quenched with 5% potassium hydrogen sulfate (20 ml)
  3. extractionextracted with ether (20 mL)
  4. dry with materialThe organic layer is then dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-806fcf5d55194585ae5f756a58dff1c8
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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