Methyl iodide → HCID 11535657, compound

Participants

Reaction Steps

To a cooled (−78° C. bath temperature) solution of 2,3-dihydro-4H-chromen-4-one (25 grams, 0.169 mole) and iodomethane (120 grams, 53 ml, 0.945 mole) in anhydrous tetrahydrofuran (1000 ml) was added portion-wise potassium tertiary butoxide (94.5 grams, 0.945 mole) over a period of 1 hour under an argon atmosphere. During this process, the reaction temperature was kept at −78° C. to avoid exothermic reaction. The cooling bath was removed, and the resulting mixture was warmed to room temperature over a period of 4 hours. The white viscous mixture was heated at 60° C. (bath temperature) for 4 hours, cooled to room temperature, and stirred at room temperature for 15 hours. The resulting mixture was poured into a mixture of diethyl ether and water. The organic layer was separated, and the aqueous layer was extracted with diethyl ether. The combined extracts were washed with saturated sodium chloride aqueous solution, dried over sodium sulfate, and concentrated. The residue was chromatographed (silica gel, elution by methylene chloride) to give 30 grams (100%) of 3,3-dimethyl-2,3-dihydro-4H-chromen-4-one as a clear pale yellow oil. Physical properties of the product were the same as those described in Example 3.

Provenance & Evidence