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

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

Participants

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

customcombined at room temperature with 500 mg
temperaturethe mixture is heated for 27 hours
temperatureunder reflux
temperaturethe solution is gradually warmed to 50° C
filtrationThe thus-precipitated product is vacuum-filtered
washwashed with water
dry with materialdried over sodium sulfate
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

Linked notes

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