(7-ethyl-3-methyl-1H-indol-2-yl)methanol → 7-ethyl-3-methyl-1H-indole-2-carbaldehyde

HRID 2097194Notes

Reaction equation

HRID 2097194 reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([CH2:12][OH:13])=[C:8]2[CH3:14])[CH3:2]>ClCCl.[O-2].[Mn+4].[O-2]>[CH2:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([CH:12]=[O:13])=[C:8]2[CH3:14])[CH3:2]

Participants

4

Reactant 1

HCID 59277628(7-ethyl-3-methyl-1H-indol-2-yl)methanol

Product 1

HCID 592775647-ethyl-3-methyl-1H-indole-2-carbaldehydeYield 65%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of (7-ethyl-3-methyl-1H-indol-2-yl)methanol (1.6 g, 9.1 mmol) and manganese (IV) oxide (3.97 g, 45.7 mmol) in dichloromethane (15 mL) was stirred overnight. The mixture was filtered through celite and evaporated to afford the title compound (1.1 mg, 65%). 1H NMR (400 MHz, CDCl3) δ 10.02 (s, 1H), 8.90 (s, 1H), 7.53 (d, J=8.0 Hz, 1H), 7.19 (d, J=7.6 Hz, 1H), 7.10 (t, J=7.7 Hz, 1H), 2.83 (q, J=7.5 Hz, 2H), 2.62 (s, 3H), 1.31 (t, J=7.5 Hz, 3H)

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-2adf64cbce204a289a6622c7cc9aa31c
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Reaction notes

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