Methyl iodide → HCID 18546294, compound

Participants

Reaction Conditions

Reaction Steps

A 1M solution of lithium hexamethyl-disilazide in tetrahydrofuran (170 ml) was added dropwise to a solution of 7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-4-(2-propenyl)chroman-2-one (32.70 g) in anhydrous tetrahydrofuran (400 ml) at −73° C. over 15 minutes under nitrogen atmosphere, followed by stirring for 30 minutes at −10° C. The reaction mixture was cooled to −75° C. and methyl iodide (10.6 ml) was added dropwise thereto over 10 minutes, followed by stirring for 10 minutes at −75° C., for 1 hour at −10° C. and then for 1 hour at 0° C. The reaction mixture was quenched with saturated aqueous ammonium chloride and partitioned between ethyl acetate and water. The organic layer was washed twice with water and dried over sodium sulfate. After concentration under reduced pressure, the resulting oil was purified by flash column chromatography (silica gel: Merck Kieselgel 60, eluent: hexane/ethyl acetate=9/1) to give (3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-(2-propenyl)chroman-2-one (30.74 g, Yield 90.8%) as a yellow oil.

Provenance & Evidence