Potassium Iodide → HCID 69589733, compound

Participants

Reaction Steps

A solution of 3-bromo-1-propanol (0.400 ml, 4.42 mmol), (+)-estrone (1.00 g, 3.70 mmol), sodium hydroxide (150 mg, 3.75 mmol) and potassium iodide (100 mg, 0.602 mmol) in 10 ml methanol and 10 ml water was refluxed overnight. The reaction mixture was shaken with 100 ml methylene chloride and 100 ml water. The organic layer was washed with a 10% NaHCO3 solution (100 ml×2) and water (100 ml×2) before drying over anhydrous Na2SO4. Further purification was performed by silica gel column chromatography with methylene chloride: acetone (50:1) as the eluent to yield 3-(2-hydroxy-propoxy)-estra-1,3,5(10)-trien-17-one (800 mg, 66%). 1H NMR spectral data, 6(CDCl3): 0.93–2.94 (m, 23H on estrone), 3.88 (2H, —CH2OH), 4.13 (t, 2H, estrone-OCH2—), 6.68–7.23 (m, 3H, aromatics).

Provenance & Evidence