(1-Benzyl-1H-indol-2-yl)methanol → 1-benzyl-1H-indole-2-carbaldehyde

HRID 1392273Notes

Reaction equation

HRID 1392273 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH2:17][OH:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4]>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:17]=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 18973468(1-Benzyl-1H-indol-2-yl)methanol

Product 1

HCID 129167171-benzyl-1H-indole-2-carbaldehydeYield 42%

Reagents, catalysts & solvents 1

HCID 178418406HCID 178418406, compoundCatalyst

Procedure

This compound was produced by modifications of the methods used by Murakami, et. al. (Tetrahedron, 1997, 53, 1593-1606) starting with (1-benzyl-1H-indol-2-yl)-methanol (1.13 g, 4.76 mmol) and manganese dioxide (5.6 g). The crude material was purified by flash chromatography through silica gel using diethyl ether/hexanes (0/100 gradient to 10/90) to give 1-benzyl-1H-indole-2-carbaldehyde (0.47 g, 42%) as an off-white solid. 1H NMR (400 MHz, CDCl3); δ 79.90 (s, 1H), 7.76 (d, 1H), 7.37 (s, 2H), 7.33 (s, 1H), 7.25-7.16 (m, 4H), 7.08 (d, 2H), 5.83 (s, 2H).

Workup

  1. customThis compound was produced by modifications of the methods
  2. customThe crude material was purified by flash chromatography through silica gel

Sources & evidence

ORD record
ord-f67e353070534e73a01b9611254aefcc
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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