Sodium Chloride → 3-(5,6-Dichloro-1H-indol-2-yl)-2-propenaldehyde

HRID 1603001Notes

Reaction equation

HRID 1603001 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([CH:12]=[CH:13][CH2:14][OH:15])=[CH:5]2.[Na+].[Cl-]>CCOCC.O=[Mn]=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[Cl:11])[NH:7][C:6]([CH:12]=[CH:13][CH:14]=[O:15])=[CH:5]2

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 540737823-(5,6-Dichloro-2-indolyl)-2-propen-1-ol

Product 1

HCID 545069833-(5,6-Dichloro-1H-indol-2-yl)-2-propenaldehydeYield 84.1%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (E) 3-(5,6-dichloro-2-indolyl)-2-propen-1-ol (13.8 g, 57.0 mmol) in Et2O (450 ml), activated MnO2 (35 g) and NaCl (35 g) were added. The reaction mixture was stirred for two days at RT, filtered on a Celite pad, washed with Et2O and dried over MgSO4 to afford (11.5 g, 47.9 mmol, yield 84.1%) of pure title compound.

Workup

  1. filtrationfiltered on a Celite pad
  2. washwashed with Et2O
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-97dc36fcef234498aa5376023d71581b
Source dataset
uspto-grants-1999_11
Patent number
US05985905

Reaction notes

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