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

HRID 2365871Notes

Reaction equation

HRID 2365871 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].I(C1C=CC=CC=1C(O)=O)(=O)=O>C(OCC)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[CH:10]=[O:11]

Participants

4

Reactant 2

HCID 98783(1H-indol-2-yl)methanolHCID 1087942-Iodoxybenzoic acid

Product 1

HCID 96389Indole-2-carboxaldehydeYield 50.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (1H-indol-2-yl)methanol (8.00 g, 54.4 mmol) and 2-iodoxybenzoic acid (“IBX”) (40.0 g, 0.163 mol) in ethyl acetate (200 mL) was stirred at 80° C. for 16 hours. The solid was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography eluting with petroleum ether/ethyl acetate (50:1) to give 1H-indole-2-carbaldehyde (4.0 g, 50% yield) as a solid. LCMS (ESI) m/z: 146.1 [M+H]+.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography
  4. washeluting with petroleum ether/ethyl acetate (50:1)

Sources & evidence

ORD record
ord-6ddf5b5433e140f588b121d9d551bd5a
Source dataset
uspto-grants-2014_04
Patent number
US08697715B2

Reaction notes

Loading…