Hydrogen Peroxide → (17beta)-13-Ethyl-3-methoxygona-1,3,5(10),15-tetraen-17-ol

HRID 328208

反応式

HRID 328208 の反応式
C1([SeH-](C2C=CC=CC=2)=[Se])C=CC=CC=1.[BH4-].[Na+].[O:17]1[C@H:19]2[C@:20]3([CH2:36][CH2:35][C@H:34]4[C@@H:25]([CH2:26][CH2:27][C:28]5[CH:29]=[C:30]([O:37][CH3:38])[CH:31]=[CH:32][C:33]=54)[C@@H:23]3[CH2:24][C@@H:18]12)[CH2:21][CH3:22].OO>C(O)C>[CH3:38][O:37][C:30]1[CH:31]=[CH:32][C:33]2[C@@H:34]3[C@H:25]([C@H:23]4[C@@:20]([CH2:36][CH2:35]3)([CH2:21][CH3:22])[C@H:19]([OH:17])[CH:18]=[CH:24]4)[CH2:26][CH2:27][C:28]=2[CH:29]=1

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 4311764Sodium borohydrideHCID 8673462416alpha,17alpha-Epoxy-3-methoxy-18-methyl-1,3,5(10)-estratrieneHCID 178528034HCID 178528034、化合物

生成物 1

HCID 86734623(17beta)-13-Ethyl-3-methoxygona-1,3,5(10),15-tetraen-17-ol

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

3.7 g. of diphenyldiselenide is dissolved in 200 ml. of absolute ethanol and combined at room temperature with 1.0 g. of sodium borohydride. After the yellow solution has lost its color, 5.0 g. of 16α,17α-epoxy-3-methoxy-18 -methyl-1,3,5(10)-estratriene is added thereto and the mixture is heated under reflux for 30 hours. The solution is then cooled to 0° C. Dropwise, 11ml. of 30% H2O2 is added to the reaction solution and the latter is then gradually heated to 50° C. After 2 hours, the solution is introduced into ice water. The precipitate is vacuum-filtered, washed with water, and taken up in methylene chloride. After chromatography on silica gel with 6-8% acetone/hexane, 1.9 g. of 3-methoxy-18-methyl-1,3,5(10),15-estratetraen-17α-ol is obtained as an oily product. [α]D 20 = -108°.

後処理

  1. customcombined at room temperature with 1.0 g
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 30 hours
  4. temperaturethe latter is then gradually heated to 50° C
  5. filtrationThe precipitate is vacuum-filtered
  6. washwashed with water

出典と根拠

ORDレコード
ord-47443581362643fe9d5aadc35279fb3a
出典データセット
uspto-grants-1977_04
特許番号
US04016269

関連ノート

読み込み中…