p-Toluenesulfonic acid → HCID 69134726, compound

Participants

Reaction Steps

3β-(p-Toluensulfonyloxy)androst-5-en-17-one (12.00 g) was added to a suspension of propane-1,3-diol (61 mL) and PTSA (610 mg) at 95° C. After stirring for 40 minutes, the mixture was cooled to room temperature, and poured in water (800 mL), bringing the pH to 7 with 5% NaHCO3. After 3 hrs the solid was filtered and dissolved in CH2Cl2. The solution was dried over Na2SO4 and evaporated to dryness under reduced pressure to give 3β-(3-hydroxypropoxy)androst-5-en-17-one (9.10 g, 97%), used without further purification. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 5.35 (1H, m), 4.34 (1H, t), 3.43 (4H, m), 3.06 (1H, m), 2.45-0.85 (21H, m), 0.96 (3H, s), 0.79 (3H, s).

Provenance & Evidence