Ethylene Glycol → 3beta-Iodoandrost-5-en-17-one-17-ethyleneketal

HRID 359351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 359351
[I:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C:11]2=[O:21])[CH2:3]1.[CH2:22](O)[CH2:23][OH:24].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH2:23]1[O:24][C:11]2([CH2:10][CH2:9][C@H:8]3[C@H:7]4[C@H:16]([CH2:15][CH2:14][C@:12]23[CH3:13])[C@:17]2([CH3:20])[C:4]([CH2:3][C@@H:2]([I:1])[CH2:19][CH2:18]2)=[CH:5][CH2:6]4)[O:21][CH2:22]1

Komponenten

5

Edukt 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 537259003beta-Iodoandrost-5-ene-17-one

Produkt 1

HCID 186444503beta-Iodoandrost-5-en-17-one-17-ethyleneketalAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

More specifically, 3β-iodoandrost-5-en-17-one (11) (11.83 g, 29.7 mmol), ethylene glycol (20 ml) and p-toluene sulfonic acid (200 mg) in benzene (250 ml) were refluxed under a Dean-Stark trap for 72 hrs. The solution was washed with saturated sodium bicarbonate, water, then dried over magnesium sulfate. Evaporation and recrystallization from ether afforded 11.5 g (87.3%) of 3β-iodoandrost-5-en-17-one-17-ethyleneketal (12): mp 140°-141° C., IR (KBr): 3010, 2940, 1470, 1425, 1375 cm-1 ; 1H NMR (CDCl3): δ5.44 (brd J=6 Hz, 1H, H-6), 3.91 (s, 4H, ketal), 1.07 (s, 3H, C-19 Me), 0.88 (s, 3H, C-18 Me); MS (m/e): 442 (M+, 1), 380 (35), 315 (57), 253 (67), 227 (11), 105 (24), 99 (100), 91 (35), 55 (27), 41 (33).

Aufarbeitung

  1. washThe solution was washed with saturated sodium bicarbonate, water
  2. dry with materialdried over magnesium sulfate
  3. customEvaporation and recrystallization from ether

Quellen und Nachweise

ORD-Eintrag
ord-de5e4cfee9194648a9e863897d0be73e
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05001119

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