Ethanol → Androsta-5,16-dien-3 beta-ol

HRID 616642

反応式

HRID 616642 の反応式
[Na].[OH:2][C@H:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C:5](=[CH:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH:11]=[C:12]2I)[CH2:4]1.C(O)C>O>[OH:2][C@H:3]1[CH2:20][CH2:19][C@@:18]2([CH3:21])[C:5](=[CH:6][CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH:11]=[CH:12]2)[CH2:4]1

参加物

5

反応物 3

HCID 702EthanolHCID 5360545Sodium2 回HCID 11069352(3S,8R,9S,10R,13S,14S)-17-iodo-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta(a)phenanthren-3-ol

生成物 1

HCID 150900Androsta-5,16-dien-3 beta-ol

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

125 g. of sodium metal were added in small portions to a stirred solution of 21 g. of 3β-hydroxy-17-iodo androsta-5,16-diene in 1.05 l. of anhydrous ethanol. During the addition the mixture was kept at reflux temperature. After all of the sodium was dissolved the reaction mixture was cooled and water was added. The ethanol was removed by distillation under reduced pressure and the resulting aqueous suspension was extracted with methyl isobutyl ketone. The extract was washed until neutral and concentrated to dryness in vacuo. The crystalline residue was recrystallized from methanol-water and 13 g. of 3β-hydroxy-androsta-5,16-diene were obtained. Two crystallizations from acetone yielded the pure compound melting at 137°-138° C. mol. peak in mass spectrum (m/e): 272.

後処理

  1. additionDuring the addition the mixture
  2. temperatureat reflux temperature
  3. temperaturewas cooled
  4. customThe ethanol was removed by distillation under reduced pressure
  5. extractionthe resulting aqueous suspension was extracted with methyl isobutyl ketone
  6. washThe extract was washed until neutral and
  7. concentrationconcentrated to dryness in vacuo
  8. customThe crystalline residue was recrystallized from methanol-water and 13 g

出典と根拠

ORDレコード
ord-0614c3ad5e564a9aa4f6399ba41cc9a6
出典データセット
uspto-grants-1978_02
特許番号
US04075233

関連ノート

読み込み中…