N-(4-iso-propylbenzenesulfonyl)-alpha-(2-n-propyl-4-hydroxymethylphenoxy)-3,4-methylenedioxyphenylacetamide → N-(4-iso-propylbenzenesulfonyl)-alpha-(4-formyl-2-n-propylphenoxy)-3,4-methylenedioxyphenyl-acetamide

Participants

Reaction Steps

To a solution of 0.573 g (1.09 mmol) of the product of Example 65 dissolved in 5.0 mL of dichloromethane was added 2.86 g (32.9 mmol) of manganese dioxide and 1.15 g of firmly powdered 3A molecular sieves and the reaction mixture was magnetically stirred at room temperature for 14 hours. The reaction mixture was then filtered through a bed of celite and MgSO4 and the filtrate was evaporated in vacuo. The residue was dissolved in dichloromethane and applied to a silica gel flash chromatography column and then eluted with 3% MeOH--CH2Cl2. Evaporation of the purified fractions and drying in vacuo afforded 0.149 g (26%) of the title compound.

Provenance & Evidence