HCID 18973381, compound → HCID 18973537, compound

HRID 2394400Notes

Reaction equation

HRID 2394400 reaction equation
[CH2:1]([C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[C:12]([CH2:17][OH:18])[CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:5][CH:4]=1)[CH3:2]>[O-2].[O-2].[Mn+4].ClCCl>[CH2:1]([C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:16]3[CH:15]=[CH:14][CH:13]=[C:12]([CH:17]=[O:18])[C:11]=3[CH:10]=[CH:9]2)=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 18973381HCID 18973381, compound

Product 1

HCID 18973537HCID 18973537, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1.00 g of 1-(4-ethylbenzyl)-4-(hydroxymethyl) indole prepared in Example 34 and 2.31 g of activated manganese dioxide (~85%), there was added 30 ml of dichloromethane and the resulting mixture was stirred at room temperature for 4 hours. The reaction solution was filtered, followed by washing with dichloromethane (50 ml×2). The solvent was distilled off, under reduced pressure, from the resulting filtrate to give 0.92 g of 1-(4-ethylbenzyl)indole-4-carbaldehyde as a yellow oily substance. The yield thereof was found to be 93%.

Workup

  1. filtrationThe reaction solution was filtered
  2. washby washing with dichloromethane (50 ml×2)
  3. distillationThe solvent was distilled off, under reduced pressure, from the resulting filtrate

Sources & evidence

ORD record
ord-99b433e2f54a45b48652419fb619f54e
Source dataset
uspto-grants-1998_09
Patent number
US05811439

Reaction notes

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