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Hydrochloric Acid → (3S,8S,9S,10R,13S,14S,16S,17R)-17-[(1R,5R)-6-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol

HRID 327771
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 327771
[CH3:1][C@H:2]1[CH2:30][O:29][C@@:5]2([O:9][C@H:8]3[CH2:10][C@H:11]4[C@@H:16]5[CH2:17][CH:18]=[C:19]6[CH2:24][C@@H:23]([OH:25])[CH2:22][CH2:21][C@:20]6([CH3:26])[C@H:15]5[CH2:14][CH2:13][C@:12]4([CH3:27])[C@H:7]3[C@@H:6]2[CH3:28])[CH2:4][CH2:3]1.Cl>[Zn].C(O)C>[OH:9][C@H:8]1[CH2:10][C@@H:11]2[C@:12]([CH3:27])([CH2:13][CH2:14][C@H:15]3[C@H:16]2[CH2:17][CH:18]=[C:19]2[C@:20]3([CH3:26])[CH2:21][CH2:22][C@H:23]([OH:25])[CH2:24]2)[C@H:7]1[C@H:6]([CH3:28])[CH2:5][CH2:4][CH2:3][C@@H:2]([CH3:1])[CH2:30][OH:29]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 99474Diosgenin

Produkt 1

HCID 11729441(3S,8S,9S,10R,13S,14S,16S,17R)-17-[(1R,5R)-6-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diolAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysator
HCID 702
Ethanol
Lösungsmittel

Versuchsvorschrift

To a 5-liter flask were sequentially added diosgenin (40 grams, 0.0965 moles, zinc dust (900 grams, -325 mesh size) and 2 liters of absolute ethanol. The suspension was then brought to reflux and 800 ml of concentrated HCl was added dropwise over a period of 2.5 hours. The reaction was refluxed for an additional 30 minutes then immediately filtered while hot, under gravity, over Whatman no. 2 filter paper to remove the zinc particles. Two liters of water was then added to the filtrate and a white precipitate formed. The mixture was cooled at room temperature and the precipitate was collected by suction filtration (Whatman no. 2 paper) and washed three times with water, then air dried to afford 35 grams (85% yield) of compound (2).

Aufarbeitung

  1. customTo a 5-liter flask were sequentially added
  2. temperatureto reflux
  3. temperatureThe reaction was refluxed for an additional 30 minutes
  4. filtrationthen immediately filtered while hot, under gravity
  5. filtration2 filter paper
  6. customto remove the zinc particles
  7. additionTwo liters of water was then added to the filtrate
  8. customa white precipitate formed
  9. filtrationthe precipitate was collected by suction filtration (Whatman no
  10. wash2 paper) and washed three times with water
  11. customair dried

Quellen und Nachweise

ORD-Eintrag
ord-b6fa099e9e494e258320e8eb3527737e
Quelldatensatz
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05274088

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