Water → HCID 12796509, compound

HRID 2049482Notes

Reaction equation

HRID 2049482 reaction equation
[H-].[Na+].[Na].[C:4]([O:7][C@@H:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[C:21](=[O:27])[CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][CH2:16][C:17]2=O)[CH2:9]1)(=O)[CH3:5].[OH2:29].O1CCC[CH2:31]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:4]([O:7][C@@H:8]1[CH2:25][CH2:24][C@@:23]2([CH3:26])[C@@H:10]([CH2:11][CH2:12][C@@H:13]3[C@@H:22]2[C:21](=[O:27])[CH2:20][C@@:18]2([CH3:19])[C@H:14]3[CH2:15][CH2:16][C:17]2=[CH2:31])[CH2:9]1)(=[O:29])[CH3:5]

Participants

7

Reactant 5

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 5360545SodiumHCID 70582546HCID 70582546, compound

Product 1

HCID 12796509HCID 12796509, compound

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Procedure

Sodium hydride (0.330 g) was carefully added to sodium dried tetrahydrofuran (10 ml) under nitrogen. Methyl triphenylphosphonium bromide (4.9 g) was added as a suspension in dry tetrahydrofuran (30 ml) followed by 3α-acetoxy-5α-androstane-11,17-dione (1.2 g) also in dry tetrahydrofuran (20 ml). The reaction mixture was refluxed for 3/4 hr. then cooled and poured into water. The product was extracted into ethyl acetate and the organic solution was washed with water, dried (Na2SO4) and evaporated. The residual oil was triturated with ether, the insoluble material was removed by filtration and the solid obtained by evaporation of the mother liquor was purified by chromatography over silica(ethyl acetate:petroleum ether 1:1) and recrystallisation from ether/petrol to give the title compound (0.695 g), m.p. 140°-1°, [α]D +44°.

Workup

  1. temperatureThe reaction mixture was refluxed for 3/4 hr
  2. temperaturethen cooled
  3. extractionThe product was extracted into ethyl acetate
  4. washthe organic solution was washed with water
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residual oil was triturated with ether
  8. customthe insoluble material was removed by filtration
  9. customthe solid obtained by evaporation of the mother liquor
  10. customwas purified by chromatography over silica(ethyl acetate:petroleum ether 1:1) and recrystallisation from ether/petrol

Sources & evidence

ORD record
ord-2e21825bd54f4d478ef9620556e7111a
Source dataset
uspto-grants-1980_04
Patent number
US04197296

Reaction notes

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