[5-(1H-indol-2-yl)-2,4-dimethoxyphenyl]methanol → 5-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde

HRID 347382Notes

Reaction equation

HRID 347382 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[C:11]([O:20][CH3:21])=[CH:12][C:13]([O:18][CH3:19])=[C:14]([CH2:16][OH:17])[CH:15]=1>C1COCC1.C(Cl)Cl.O=[Mn]=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[C:11]([O:20][CH3:21])=[CH:12][C:13]([O:18][CH3:19])=[C:14]([CH:15]=1)[CH:16]=[O:17]

Participants

5

Reactant 1

HCID 21082531[5-(1H-indol-2-yl)-2,4-dimethoxyphenyl]methanol

Product 1

HCID 161156215-(1H-indol-2-yl)-2,4-dimethoxybenzaldehydeYield 90.6%

Reagents, catalysts & solvents 3

HCID 14801Manganese dioxideCatalyst2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [5-(1H-indol-2-yl)-2,4-dimethoxyphenyl]methanol (Ex-57C, 5.8 g, 20 mmol) in 250 ml of THF and 250 ml of CH2Cl2, was added MnO2 (1.8 g, 20 mmol). The mixture was heated to reflux. The reaction was pushed to completion by adding two more portions of MnO2 (1.8 g each ) within 48 h. The mixture was then cooled to room temperature and filtered. The filtrate was concentrated and the residue was recrystallized from EtOAc/Hexane to give 5.1 g (88%) of 5-(1H-indol-2-yl)-2,4-dimethoxybenzaldehyde. 1H-NMR (300 MHz, DMSO-d6) δ 11.29 (br s, 1H), 10 24 (s, 1H), 8.10 (s, 1H), 7.47 (d, J=8 Hz, 1H), 7.37 (d, J=7 Hz, 1H), 7.01–7.05 (m, 1H), 6.91–6.95 (m, 1H), 6.85–6.86 (m, 2H), 4.06 (s, 3H), 3.99 (s, 3H). HRMS (EI) Calcd. for C17H15NO3: 281.1052 (M+); Found: 281.1046.

Workup

  1. temperatureThe mixture was heated to reflux
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe residue was recrystallized from EtOAc/Hexane

Sources & evidence

ORD record
ord-ca679779245b44fe92afe92c10ae873b
Source dataset
uspto-grants-2007_02
Patent number
US07173129B2

Reaction notes

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