Aluminium lithium hydride → 3-Indol-1-yl-3-phenyl-propan-1-ol

HRID 250192Notes

Reaction equation

HRID 250192 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]([N:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:12]1([CH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH2:4][CH2:3][OH:2])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 580885583-Indol-1-yl-3-phenyl-propionic acid methyl ester

Product 1

HCID 235559373-Indol-1-yl-3-phenyl-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-indol-1-yl-3-phenyl-propionic acid methyl ester (0.2 g, 0.71 mmol) in THF (5 mL) at 0° C. was added 1M LiAlH4 in THF (0.71 mL), and the mixture was stirred for 0.5 hours at room temperature. The reaction mixture was quenched by the cautious addition of Na2SO4.10H2O and the reaction mixture was stirred for another 1 h at room temperature. The mixture was filtered and the solvent was removed under vacuum. 3-Indol-1-yl-3-phenyl-propan-1-ol was obtained as a clear oil (0.166 g, 92% yield).

Workup

  1. customThe reaction mixture was quenched by the cautious addition of Na2SO4.10H2O
  2. stirringthe reaction mixture was stirred for another 1 h at room temperature
  3. filtrationThe mixture was filtered
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-20521d03cec147bc9bf3d6ddd096cf03
Source dataset
uspto-grants-2011_01
Patent number
US07863305B2

Reaction notes

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