Hydrochloric Acid → Cholesta-5,7-diene-1,3-diol

HRID 1196399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1196399
[H-].[Al+3].[Li+].[H-].[H-].[H-].CS(O[CH:12]([C@H:18]([C@@H:20]1[C@:37]2([CH3:38])[C@H:23]([C:24]3[C@H:34]([CH2:35][CH2:36]2)[C@:32]2([CH3:33])[C:27]([CH2:28][C@@H:29]([O:46]C4CCCCO4)[CH2:30][C@@H:31]2[O:39]C2CCCCO2)=[CH:26][CH:25]=3)[CH2:22][CH2:21]1)[CH3:19])[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])(=O)=O.Cl>O1CCCC1.O>[CH3:17][CH:15]([CH2:14][CH2:13][CH2:12][C@H:18]([C@@H:20]1[C@:37]2([CH3:38])[C@H:23]([C:24]3[C@H:34]([CH2:35][CH2:36]2)[C@:32]2([CH3:33])[C:27]([CH2:28][C@@H:29]([OH:46])[CH2:30][C@@H:31]2[OH:39])=[CH:26][CH:25]=3)[CH2:22][CH2:21]1)[CH3:19])[CH3:16]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydrideHCID 867458381alpha,3beta-Bis(tetrahydropyran-2-yloxy)cholesta-5,7-dien-22-yl methanesulfonate

Produkt 1

HCID 193829Cholesta-5,7-diene-1,3-diolAusbeute 45,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 0.10 g of lithium aluminum hydride in 5 ml of tetrahydrofuran was added 0.66 g of 1α,3β-bis(tetrahydropyran-2-yloxy)cholesta-5,7-dien-22-yl methanesulfonate under heating and the mixture was refluxed for 2 hours. The resulting reaction mixture was cooled and, then, water and diluted hydrochloric acid were added in succession. The mixture was stirred at room temperature for 2 hours. The resulting solution was diluted with water and extracted with diethyl ether. The extract was washed with diluted hydrochloric acid and aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The low-boiling fraction was then distilled off and the residue was purified by silica gel column chromatography and recrystallized from methanol. The procedure yielded 0.18 g of cholesta-5,7-diene-1α,3β-diol (yield: 45%) showing the following physical properties.

Aufarbeitung

  1. temperatureunder heating
  2. temperaturethe mixture was refluxed for 2 hours
  3. customThe resulting reaction mixture
  4. temperaturewas cooled
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with diluted hydrochloric acid and aqueous sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe low-boiling fraction was then distilled off
  9. customthe residue was purified by silica gel column chromatography
  10. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-bceb443ccc514b358e4e50f418154551
Quelldatensatz
uspto-grants-1992_05
Patentnummer
US05112998

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