(1H-indol-2-yl)methanol → Indole-2-carboxaldehyde

HRID 259823

Reaction equation

HRID 259823 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH2:10][OH:11]>C(Cl)Cl.O=[Mn]=O>[CH:10]([C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:11]

Participants

4

Reactant 1

HCID 98783(1H-indol-2-yl)methanol

Product 1

HCID 96389Indole-2-carboxaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

A total of 1.76 g of 2-indolemethanol was dissolved in dry CH2Cl2 (20 mL) at room temperature and stirred overnight with MnO2 (2.1 g, 24 mmol). The mixture was filtered through Celite, the filtrate was evaporated under reduced pressure, and the product was purified by flash chromatography (CH2Cl2). Yield: 1.31 g (75%), 1H NMR (CDCl3): δ7.1-7.5 (m, 4H), 7.76 (d, 1H, J=7.8 Hz), 9.41 (br s, 1H), 9.86 (s, 1H).MS EI): m/z 145 (M+).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customthe filtrate was evaporated under reduced pressure
  3. customthe product was purified by flash chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-60ef377f2f62446ba45f801c0bb4075c
Source dataset
uspto-grants-1996_06
Patent number
US05523411

Linked notes

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