Hydrochloric Acid → HCID 70502921, compound

Reaction equation

[Cl:1][C@H:2]1[CH2:20][C@@:17]2([CH2:18][CH3:19])[C@@H:13]([C@@H:14]([OH:22])[CH2:15][C:16]2=[O:21])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][CH2:11]2)=[CH:8][C:7](=[O:23])[CH2:6][CH2:5]1.[C:24](OC(=O)C)(=[O:26])[CH3:25].Cl>N1C=CC=CC=1>[C:24]([O:22][C@@H:14]1[C@H:13]2[C@H:12]3[C@H:3]([C@H:2]([Cl:1])[CH2:20][C@:17]2([CH2:18][CH3:19])[C:16](=[O:21])[CH2:15]1)[C@@H:4]1[C:9](=[CH:8][C:7](=[O:23])[CH2:6][CH2:5]1)[CH2:10][CH2:11]3)(=[O:26])[CH3:25]

Participants

Procedure

1.6 g of 11β-chloro-15α-hydroxy-18-methyl-4-estrene-3,17-dione in 5 ml of pyridine is stirred at room temperature under argon with 1.2 ml of acetic anhydride. After 18 hours, the solution is introduced into hydrochloric-acid-containing ice/water. The thus-precipitated product is vacuum-filtered, dissolved in ethyl acetate, and washed with water. Recrystallization of the crude product from isopropyl ether yields 1.0 g of 15α-acetoxy-11α-chloro-18-methyl-4-estrene-3,17-dione, mp 125.0° C.