Methane → HCID 54395952, compound

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Reaction Steps

To 10 mL of dry dimethylformamide in a flask cooled with an ice bath was added dropwise with stirring phosphoryl chloride (1.76 g, 0.0115 mole). After a few minutes 3,3-diisobutyl-1,2-dimethyl-(3H)-indolium iodide (3.85 g, 0.01 mole) was added portionwise over 5 min. The resulting solution was allowed to stir at room temperature for at least 3 hours. This solution was then slowly poured into 250 mL of water stirring in a beaker. After a few minutes 3,3-diisobutyl-2-dimethylaminovinyl-1-methyl-(3H)-indolium iodide separated as its monohydrate via elemental analysis and NMR of a small sample which was removed. This aqueous suspension was then heated to boiling with stirring to dissolve this intermediate product giving a yellow solution with a little purple scum floating on the top. A little Norit was added and after a minute or so the solution was filtered. The yellow filtrate was made strongly basic with 20% sodium hydroxide solution and stirred with warming at 50°-60° C. for a few minutes. The formylmethylene product separated and slowly became crystalline. After cooling to room temperature, the product was filtered, washed well with water, and dried to give 2.3 g (80.6%). The IR and NMR were good. (MW 285.43)

Provenance & Evidence