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

HRID 328211

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HRID 328211 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 1049Pyridine용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3a53b1c9d5d9446396137f3bc65b4bf9
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04016269

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