Isopropanol → HCID 66859480, compound

Participants

Reaction Steps

KH 30% in oil (89.98 mmol) was suspended in THF (50 ml), under N2 atmosphere. 17-Allyl-3-(benzyloxy)-2-ethoxy-estra-1,3,5(10)-trien-17-ol (7.7 g, 17.30 mmol) and 18-Crown-6 (88.25 mmol) were dissolved in THF (200 ml) and added dropwise in 40 min. The mixture was stirred for 3 h at RT. The mixture was carefully poured into IPA via canula. The mixture was poured into aq. sat. NH4Cl (1 l). The water layer was extracted with EtOAc (3×250 ml). The combined organic layers were washed with brine (1×500 ml), dried over Na2SO4 and concentrated in vacuo. Purification via filtration over Silica (eluens heptan to 40% DCM in heptan) provided 4.2 g (9.51 mmol, 55%) of (XXX-(C2-D)-2c).

Provenance & Evidence