Methyl iodide → HCID 69283487, compound

Participants

Reaction Steps

i)—A solution of lithium bis(trimethylsilyl)amide (55.5 mmol) in tetrahydrofuran (96 ml) was cooled to 40° C. A solution of (7α,14β)-3-methoxy-7-methylestra-1,3,5(10)-trien-17-one (Example 4, step ii; 15.0 g) in dry tetrahydrofuran (66 ml) was added dropwise and the reaction mixture was stirred for 45 min. Then, at −30° C., iodomethane (6.3 ml) was added and stirring was continued for 1 h (−30<T −20° C.). The mixture was poured into a saturated aqueous solution of ammonium chloride and the product was extracted into ethyl acetate. The combined organic phases were washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure, to give (7α,14β,16β)-3-methoxy-7,16-dimethylestra-1,3,5(10)-trien-17-one (17.33 g). The product was used in the following step without further purification.

Provenance & Evidence