HCID 13564274, compound → HCID 70478112, compound

Participants

Reaction Steps

(E)-11-(Fluoromethylene)estr-4-en-17-one (XII, Example 55, 382 ml) is cooled on an ice bath. Propynyl magnesium bromide (about 0.5M, 4.24 ml is THF) is added and the mixture stirred. After 2 hr TLC shows a small amount of starting material and an additional Grignard reagent is added (0.5 ml). After another 0.5 hr ice and water are added and the product extracted with ether, washed several times with water, dried over sodium sulfate, filtered, and concentrated. The residue is chromatographed over a silica gel column using ethyl acetate/hexane (10/90) as the irrigant. Fractions 39 to 45 are pooled and concentrated to give a solid which is crystallized from methanol/water to give the title compound; NMR (CDCl3) 0.83, 1.86, 5.47, 6.53 δ; MS (m/e) 328, 313, 295 and 246; IR (mull) 3428, 1677 cm-1.

Provenance & Evidence