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

HRID 359351노트

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HRID 359351 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-de5e4cfee9194648a9e863897d0be73e
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05001119

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