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

HRID 328209
Notes
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Reaction equation

HRID 328209 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([CH2:35][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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e0bfc620d4834f2c86ce4fb8e416b3b7
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