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

HRID 371828노트

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HRID 371828 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-70411f430a4740aa990002bf750fbbba
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04087524

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