3-(4-Chlorophenyl)-3-(3-pyridyl)-2-propen-1-ol → 3-(4-Chlorophenyl)-3-(3-pyridyl)-2-propenal

HRID 1649543Notes

Reaction equation

HRID 1649543 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:9][CH2:10][OH:11])=[CH:4][CH:3]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:9][CH:10]=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 537919533-(4-Chlorophenyl)-3-(3-pyridyl)-2-propen-1-ol

Product 1

HCID 543261733-(4-Chlorophenyl)-3-(3-pyridyl)-2-propenalYield 100.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

A mixture of 0.30 g 3-(4-chlorophenyl)-3-(3-pyridyl)-2-propen-1-ol and 1.5 g manganese dioxide in 15 ml chloroform was stirred overnight at room temperature under nitrogen. Filtration and evaporation of the solvent gave 0.30 g of a yellow oil, which contained the isomeric aldehydes in a Z/E ratio of circa 60/40 according to NMR. The crude product was used directly in the reductive dimethylamination according to Example 15.

Workup

  1. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-9ecc444cc209468e8b37b6e4fda436d5
Source dataset
uspto-grants-1983_11
Patent number
US04418065

Reaction notes

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