Methyl 3-(1-methylindol-3-YL)propanoate → 3-(1-Methyl-1H-indol-3-yl)propan-1-ol

HRID 50992Notes

Reaction equation

HRID 50992 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][C:13](OC)=[O:14])=[CH:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][CH2:12][CH2:13][OH:14])=[CH:3]1

Participants

4

Reactant 2

HCID 13679809Methyl 3-(1-methylindol-3-YL)propanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 227358873-(1-Methyl-1H-indol-3-yl)propan-1-olYield 96%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3-(1-methyl-3-indolyl)propionate (300 mg, 1.38 mmol) in Et2O (3.0 mL) was added LiAlH4 at 0° C. under N2 atmosphere. The reaction mixture was stirred for 30 min at 0° C. and quenched by careful addition of H2O. EtOAc was added to the quenched reaction mixture. The organic layer was separated, washed with brine and dried over MgSO4. It was then concentrated in vacuo and chromatographed on a silica gel column by elution with EtOAc/Hexanes to give 3-(1-methyl-3-indolyl)-1-propanol (250 mg, 96%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ1.28 (t, 1H, J=6.2 Hz), 1.98 (qu, 2H, J=7.7 Hz), 2.85 (t, 2H, J=7.3 Hz), 3.70-3.78 (m, 4H), 6.86 (s, 1H), 7.10 (dt, 1H, J=1.1, 7.0 Hz), 7.22 (dt, 1H, J=1.1, 7.5 Hz), 7.29 (d, 1H, J=8.1 Hz), 7.60 (d, 1H, J=7.7 Hz) ppm.

Workup

  1. customquenched by careful addition of H2O
  2. additionEtOAc was added to the quenched reaction mixture
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationIt was then concentrated in vacuo
  7. customchromatographed on a silica gel column by elution with EtOAc/Hexanes

Sources & evidence

ORD record
ord-3039d00c888c4f88a1e473c279218273
Source dataset
uspto-grants-2004_03
Patent number
US06713471B1

Reaction notes

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