p-Toluenesulfonic acid → 17beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one 3-ethylenethioketal

HRID 1834913ノート

反応式

HRID 1834913 の反応式
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:19]([CH2:20][CH2:21][C@:3]12[CH3:4])[C@:16]1([CH2:17][OH:18])[C:11](=[CH:12][C:13](=[O:23])[CH2:14][C@@H:15]1[CH3:22])[CH2:10][CH2:9]3.[CH:24](S)([SH:26])[CH3:25].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)(=O)C>[CH2:25]1[O:23][C:13]2([CH2:14][C@H:15]([CH3:22])[C@@:16]3([CH2:17][OH:18])[C:11]([CH2:10][CH2:9][C@@H:8]4[C@@H:19]3[CH2:20][CH2:21][C@@:3]3([CH3:4])[C@H:5]4[CH2:6][CH2:7][C@@H:2]3[OH:1])=[CH:12]2)[S:26][CH2:24]1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 336451,1-EthanedithiolHCID 2279742517beta,19-Dihydroxy-1alphamethyl-4-androsten-3-one

生成物 1

HCID 2279742417beta,19-Dihydroxy-1alpha-methyl-4-androsten-3-one 3-ethylenethioketal

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

17β,19-Dihydroxy-1α-methyl-4-androsten-3-one in acetic acid is treated with ethanedithiol and p-toluenesulfonic acid. After standing about 4 hours at room temperature, the solution is poured onto water and the mixture extracted with methylenechloride. The methylenechloride extract is washed well with water, sodium hydroxide solution, water, dried over sodium sulfate and evaporated under reduced pressure to leave 17β,19-dihydroxy-1α-methyl-4-androsten-3-one 3-ethylenethioketal which is recrystallized once from acetone-hexane.

後処理

  1. additionthe solution is poured onto water
  2. extractionthe mixture extracted with methylenechloride
  3. extractionThe methylenechloride extract
  4. washis washed well with water, sodium hydroxide solution, water
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-be57ad11a4a4418a932f8ae6b986875e
出典データセット
uspto-grants-1978_01
特許番号
US04071624

反応ノート

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