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

HRID 328208

반응식

HRID 328208 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
0 °C

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-47443581362643fe9d5aadc35279fb3a
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04016269

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