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

HRID 328209

反応式

HRID 328209 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([CH2:35][CH2:34][C@H:33]4[C@@H:24]([CH2:25][CH2:26][C:27]5[CH:28]=[C:29]([O:36][CH3:37])[CH:30]=[CH:31][C:32]=54)[C@@H:22]3[CH2:23][C@@H:18]12)[CH3:21].OO>C(O)C>[CH3:37][O:36][C:29]1[CH:30]=[CH:31][C:32]2[C@@H:33]3[C@H:24]([C@H:22]4[C@@:20]([CH2:35][CH2:34]3)([CH3:21])[C@H:19]([OH:17])[CH:18]=[CH:23]4)[CH2:25][CH2:26][C:27]=2[CH:28]=1

参加物

6

反応物 4

HCID 784Hydrogen PeroxideHCID 4311764Sodium borohydrideHCID 1257692916alpha,17alpha-Epoxy-3-methoxy-1,3,5(10)-estratrieneHCID 178528034HCID 178528034、化合物

生成物 1

HCID 227968373-Methoxy-1,3,5(10),15-estratetraen-17alpha-ol

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

1.9 g. of diphenyldiselenide is dissolved in 100 ml. of absolute ethanol and combined at room temperature with 500 mg. of sodium borohydride. After decolorization of the yellow solution, 2.5 g. of 16α,17α-epoxy-3-methoxy-1,3,5(10)-estratriene [B. Schoenecker et al., Z.Chem [Chemical News] 10 (6), (1910)] is added thereto, and the mixture is heated for 27 hours under reflux. After cooling to 0° C., 6 ml. of 30% H2O2 is added dropwise thereto, and the solution is gradually warmed to 50° C. After 2 hours, the solution is poured into ice water. The thus-precipitated product is vacuum-filtered, washed with water, taken up in methylene chloride, and dried over sodium sulfate. After the crude product has been chromatographed on silica gel with 5 - 7.5% acetone/hexane, 1.1 g. of 3-methoxy-1,3,5(10),15-estratetraen-17α-ol is isolated as an oily product.

後処理

  1. customcombined at room temperature with 500 mg
  2. temperaturethe mixture is heated for 27 hours
  3. temperatureunder reflux
  4. temperaturethe solution is gradually warmed to 50° C
  5. filtrationThe thus-precipitated product is vacuum-filtered
  6. washwashed with water
  7. dry with materialdried over sodium sulfate
  8. customAfter the crude product has been chromatographed on silica gel with 5 - 7.5% acetone/hexane, 1.1 g

出典と根拠

ORDレコード
ord-e0bfc620d4834f2c86ce4fb8e416b3b7
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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