Hydrogen Peroxide → 3-Acetoxy-1,3,5(10),15-estratetraen-17alpha-ol

HRID 328211

反応式

HRID 328211 の反応式
C1([SeH-](C2C=CC=CC=2)=[Se])C=CC=CC=1.[BH4-].[Na+].[C:17]([O:20][C:21]1[CH:38]=[CH:37][C:36]2[C@@H:35]3[C@H:26]([C@H:27]4[C@@:31]([CH2:33][CH2:34]3)([CH3:32])[C@@H:30]3[O:39][C@@H:29]3[CH2:28]4)[CH2:25][CH2:24][C:23]=2[CH:22]=1)(=[O:19])[CH3:18].OO.C(OC(=O)C)(=O)C>N1C=CC=CC=1.C(O)C>[C:17]([O:20][C:21]1[CH:38]=[CH:37][C:36]2[C@@H:35]3[C@H:26]([C@H:27]4[C@@:31]([CH2:33][CH2:34]3)([CH3:32])[C@H:30]([OH:39])[CH:29]=[CH:28]4)[CH2:25][CH2:24][C:23]=2[CH:22]=1)(=[O:19])[CH3:18]

参加物

8

反応物 5

HCID 784Hydrogen PeroxideHCID 7918Acetic AnhydrideHCID 4311764Sodium borohydrideHCID 227968363-Acetoxy-16alpha,17alpha-epoxy-1,3,5(10)-estratrieneHCID 178528034HCID 178528034、化合物

生成物 1

HCID 227968353-Acetoxy-1,3,5(10),15-estratetraen-17alpha-ol

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

1.7 g. of diphenyldiselenide is dissolved in 90 ml. of absolute ethanol and mixed at room temperature with 480 mg. of sodium borohydride. After decolorization of the yellow solution, 2.2 g. of 3-acetoxy-16α,17α-epoxy-1,3,5(10)-estratriene [V. Prelog et al., Helv. 28, 250 (1945)] is added thereto and the mixture heated for 20 hours under reflux. After cooling to 0° C., 5 ml. of 30% H2O2 is added dropwise, and the solution is gradually warmed to 50° C. The product is worked up in accordance with Example 3, and then an after-acetylation is carried out in 5 ml. of pyridine with 2.5 ml. of acetic anhydride. The reaction solution is introduced into ice water. The thusprecipitated product is vacuum-filtered, washed with water, dissolved in methylene chloride, and dried over sodium sulfate. By chromatography of the crude product on silica gel with acetone/hexane, 930 mg. of 3-acetoxy-1,3,5(10),15-estratetraen- 17α-ol is obtained.

後処理

  1. temperaturethe mixture heated for 20 hours
  2. temperatureunder reflux
  3. temperaturethe solution is gradually warmed to 50° C
  4. filtrationThe thusprecipitated product is vacuum-filtered
  5. washwashed with water
  6. dissolutiondissolved in methylene chloride
  7. dry with materialdried over sodium sulfate

出典と根拠

ORDレコード
ord-3a53b1c9d5d9446396137f3bc65b4bf9
出典データセット
uspto-grants-1977_04
特許番号
US04016269

関連ノート

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