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

HRID 1733088ノート

反応式

HRID 1733088 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 4 hours at room temperature, the solution is poured onto water and the mixture extracted with methylenechloride. The methylenechloride extracts are 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 a solution of acetone-hexane.

後処理

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

出典と根拠

ORDレコード
ord-a7529caf3192447e84ae3f0ac0148214
出典データセット
uspto-grants-1980_12
特許番号
US04239681

反応ノート

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