HCID 23003154, compound → HCID 23003156, compound

HRID 396209Notes

Reaction equation

HRID 396209 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH2:17][C:18]#[N:19])[C:10]([CH2:20][OH:21])=[CH:9]2>C(Cl)Cl.O=[Mn]=O>[Cl:1][C:2]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][CH2:16][CH2:17][C:18]#[N:19])[C:10]([CH:20]=[O:21])=[CH:9]2

Participants

4

Reactant 1

HCID 23003154HCID 23003154, compound

Product 1

HCID 23003156HCID 23003156, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[5-(2,6-dichlorobenzyloxy)-2-hydroxymethyl-indol-1-yl]butyronitrile (1.73 g, 4.44 mmol) in CH2Cl2 (100 mL) was added MnO2 (3.09 g, 35.6 mmol) and the reaction was stirred at room temperature for 18 h. The reaction mixture was filtered through Celite and the filtrate was concentrated under reduced pressure. Purification by flash column chromatography (silica gel, ethyl acetate/hexane) yielded the desired aldehyde (1.25 g, 73%) as a white solid. MS(ES) m/e 387.0 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customPurification by flash column chromatography (silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e795fffa4dda40c8bdc15ab4bd1fc4e4
Source dataset
uspto-grants-2003_08
Patent number
US06608059B1

Reaction notes

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