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

HRID 359351Notes

Reaction equation

HRID 359351 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 186444503beta-Iodoandrost-5-en-17-one-17-ethyleneketalYield 87.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-de5e4cfee9194648a9e863897d0be73e
Source dataset
uspto-grants-1991_03
Patent number
US05001119

Reaction notes

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