Sodium Iodide → Methyl 2-acetyl-7-(3-bromopropoxy)-8-n-propylchroman-2-carboxylate

Participants

Reaction Steps

A 50 ml single neck round bottom flask was charged with 640 mg (2.2 mmole) of the compound from Example 39, 6.63 g or 3.33 ml (32.8 mmole) of 1,3-dibromopropane, 690 mg (5 mmole) of anhydrous potassium carbonate, 150 mg (1 mmole) of sodium iodide, and 4 ml of methyl ethyl ketone. The flask was equipped with a magnetic stirring bar and a condenser topped with a calcium chloride drying tube, and refluxed with stirring for 72 hours. The insoluble solids were removed by filtration and the filtrate was concentrated by rotary evaporation. Purification of the residual oil by high pressure liquid chromatography (15% ethyl acetate-hexane) gave 400 mg (44%) of the title compound as a clear oil, homogenous by this layer chromatrography (20% ethyl acetate-hexane).

Provenance & Evidence