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

HRID 1362445Notes

Reaction equation

HRID 1362445 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-ba9849323a19496ba81e3a24ad1c1fbf
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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