Diethyl Ether → (E)-3-(5,6-Dichloroindol-2-yl)-2-propenaldehyde

HRID 1070696Notes

Reaction equation

HRID 1070696 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.C(OCC)C.[Na+].[Cl-]>>[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

4

Reactant 3

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 540737823-(5,6-Dichloro-2-indolyl)-2-propen-1-ol

Product 1

HCID 10823931(E)-3-(5,6-Dichloroindol-2-yl)-2-propenaldehydeYield 89%

Procedure

To a solution of (E) 3-(5,6-dichloroindol-2-yl)-2-propen-1-ol (23.8 g, 98.3 mmol) in diethyl ether (800 ml) activated MnO2 (71 g, 8.76 mol) and NaCl (60 g) were added and the resulting suspension stirred for one day at RT. It was then filtered on a Celite pad repeatedly washed with AcOEt and the organic phase dried (MgSO4) and evaporated to give 21.0 g of the title compound (87.5 mmol, yield 89.0%) that was used as such in the next step.

Workup

  1. filtrationIt was then filtered on a Celite pad
  2. washrepeatedly washed with AcOEt
  3. dry with materialthe organic phase dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-4f8b37c8b9984d3383023638a651ad23
Source dataset
uspto-grants-2005_06
Patent number
US06903117B2

Reaction notes

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