1,2-Dichloroethane → 17-Hydroxyprogesterone

Participants

Reaction Steps

To a stirred solution of 16-dehydroprogesterone 3 (0.041 g, 0.131 mmol, 1.0 equ) and Mn(dpm)3 (0.002 g, 0.003 mmol, 0.02 eq) in a mixture of isopropanol (1.5 mL) and enough 1,2-dichloroethane (0.6 mL) to completely dissolve the starting material at 0° C. for 20 min. then at room temperature for 2 h under O2. The solvents were removed by distillation under reduced pressure, affording a cream solid. Purification by flash column chromatography over silica, eluting with 30% EtOAc-hexanes afforded the 17 α-hydroxyprogesterone 4 as a white crystalline solid (0.037 g, 85%) which was identical in all respects with an authentic sample.

Provenance & Evidence