Acetate → Estra-4,16-dien-3-one

Participants

Reaction Steps

This synthesis is depicted in FIG. 11. 19-Nor-testosterone (XIX) is commercially available, e.g., from Chemical Dynamics Corp. It provides the starting material for 19-Nor-16-androstene derivatives. 19-Nor-testosterone (XIX) was converted into the acetate (Hartman, J. A. et al., J. Am. Chem. Soc. (1956) 78: 5662) with acetanhydride and pyridine. (a) A solution of this acetate (4.8 g, 15.17 mmol) in toluene (10 ml) was pyrolyzed (b) at 5400 (200 Torr, slow N2 -stream) in a glass tube packed with quartz pieces. Chromatography of the crude pyrolysate (3.1 g) on silica gel (150 g) with CH2Cl2 gave 1.1 g (28%) of the homogenous oily ketone 9; +57.9° (C 1) ((27!: m.p. 71-73°).--IR. (CHCl3): 1660s, 1615m, 1585w,--1H-NMR. (90 MHz): 0.84 (s, 3 H); 5.82 (m, 2 H); 5.87 (br. s, 1 H).

Provenance & Evidence