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Trifluoromethanesulfonic acid → HCID 45100641, Verbindung

HRID 2393214
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2393214
[CH3:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][C@H:10](OS(C(F)(F)F)(=O)=O)[C:11]2=[O:21])[CH2:3]1.C[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3C[C@H](O)C2=O)C1.FC(F)(F)S(O)(=O)=O.[Cl-:60].[Li+]>CN(C=O)C.O>[CH3:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][C@@H:10]([Cl:60])[C:11]2=[O:21])[CH2:3]1
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Komponenten

7

Edukt 4

HCID 62406Trifluoromethanesulfonic acidHCID 433294Lithium ChlorideHCID 67653530HCID 67653530, VerbindungHCID 86743737HCID 86743737, Verbindung

Produkt 1

HCID 45100641HCID 45100641, VerbindungAusbeute 96,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

800 mg of 3β-methyl-16β-trifluoromethylsulfonyloxy-5-androsten-17-one, prepared from 3β-methyl-16β-hydroxy-5-androsten-17-one and trifluoromethane sulfonic acid was placed in 16 ml DMF and was treated with 100 mg Lithium chloride at room temperature. The reaction mixture was stirred magnetically for 21 hours. Water is then added and the resulting crystalline ppt was collected. The crystals were washed with additional water and were then dissolved in CH2Cl2, filtered through anhydrous sodium sulfate and the solvent was evaporated off. The resulting crystals were recrystallized from CH3OH, yielding 570 mg of final product. m.p. 159°-165° C.

Aufarbeitung

  1. customthe resulting crystalline ppt was collected
  2. washThe crystals were washed with additional water
  3. dissolutionwere then dissolved in CH2Cl2
  4. filtrationfiltered through anhydrous sodium sulfate
  5. customthe solvent was evaporated off
  6. customThe resulting crystals were recrystallized from CH3OH

Quellen und Nachweise

ORD-Eintrag
ord-5ad1da4e6b2244aaa6945c20c0327bde
Quelldatensatz
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05804576

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