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

HRID 1764868Notes

Reaction equation

HRID 1764868 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-316ac458b72d4cf5bab1c1ba6845173c
Source dataset
uspto-grants-2007_06
Patent number
USRE039679E1

Reaction notes

Loading…