4-Toluenesulfonyl chloride → 3beta-Toluene-p-sulphonyloxy-5alpha-pregn-16-ene-11,20-dione
Reaktionsgleichung
[OH:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:18]2[C:17](=[O:23])[CH2:16][C@@:15]2([CH3:24])[C@H:8]3[CH2:9][CH:10]=[C:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1>N1C=CC=CC=1>[C:25]1([CH3:35])[CH:30]=[CH:29][C:28]([S:31]([O:1][C@H:2]2[CH2:21][CH2:20][C@@:19]3([CH3:22])[C@@H:4]([CH2:5][CH2:6][C@@H:7]4[C@@H:18]3[C:17](=[O:23])[CH2:16][C@@:15]3([CH3:24])[C@H:8]4[CH2:9][CH:10]=[C:11]3[C:12](=[O:14])[CH3:13])[CH2:3]2)(=[O:33])=[O:32])=[CH:27][CH:26]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 3β-hydroxy-5α-pregn-16-ene-11,20-dione (39.6 g) in dry pyridine (165 ml.) was treated with toluene-p-sulphonyl chloride (43.9 g.) to give 3β-toluene-p-sulphonyloxy-5α-pregn-16-ene-11,20-dione (56.7 g.) m.p. 147°-151°. A portion (10.7 g.) of this material was crystallised from ethyl acetate-petrol to give the pure toluenesulphonate (9.2 g.) as plates m.p. 154°-155°, [α]D + 42.8° (c 1.2).