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

HRID 328208
Notes
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Reaction equation

HRID 328208 reaction equation
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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Conditions

Temperature
0 °C

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-47443581362643fe9d5aadc35279fb3a
Source dataset
uspto-grants-1977_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04016269

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes