Acetone → HCID 14329713, compound

Participants

Reaction Steps

A mixture of the crude methanesulfonate from Example 14 (about 0.932 mmole), 595 mg of sodium iodide, and 5 ml of acetone was stirred at room temperature for 43.5 hours then treated with water and worked-up with ether in the usual manner (the ether extracts were additionally washed with dilute sodium bisulfite solution). The oily product (390 mg) was chromatographed on 20 g of silica gel. Elution with 19:1 and 9:1 hexane-ethyl acetate afforded 306 mg (76.0%) of racemic-3,4-dihydro-2,5,7,8-tetramethyl-6-(3-iodopropoxy)-2H-1-benzopyran-2-carboxylic acid methyl ester as a colorless oil. In another experiment, iodide prepared in this way crystallized to a solid, mp 73°-75.5° C.

Provenance & Evidence