Réaction #43635

Équation de réaction

7-ethenyl-2-methyl-3,4-dihydro-1(2H)-isoquinolinone

sodium periodate

→

product

Rendement 74.3%

2-methyl-1-oxo-1,2,3,4-tetrahydro-7-isoquinolinecarbaldehyde

Rendement 74.3%

Solvants

1,4-dioxane

1,4-dioxane

water

Conditions de réaction

Traitement

1. 1
   Autreevaporated again
2. 2
   workup.DISSOLUTIONThe mixture was then dissolved in dichloromethane (100 ml)
3. 3
   Séchagedried with magnesium sulphate
4. 4
   Autreevaporated
5. 5
   LavageChromatography on silica, eluting with 0-100% Ethyl Acetate/Hexane

Mode opératoire

To a solution of 7-ethenyl-2-methyl-3,4-dihydro-1(2H)-isoquinolinone (181 mg, 0.968 mmol) in 1,4-dioxane (I 5 ml) and water (3 ml) at 0° C. was added sodium periodate (476 mg, 2.226 mmol) and osmium tetroxide (1.1 ml of a 4% aqueous solution). The reaction mixture was warmed to room temperature and stirred for 0.5 h before evaporation of the reaction mixture. The residue was dissolved in 1,4-dioxane (20 ml) and evaporated again. The mixture was then dissolved in dichloromethane (100 ml), dried with magnesium sulphate and evaporated. Chromatography on silica, eluting with 0-100% Ethyl Acetate/Hexane, gave the product (136 mg, 74%).

Source