Reaktion #459008

ord-0d06e6505c2c4bc38a1a215cd98f8202

Reaktionsgleichung

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43CO)[C@@H]1CCC2=O
19-Hydroxy-4-androstene-3,17-dione
CC(C)(C)[Si](C)(C)Cl
t-butyldimethylsilylchloride
c1ccncc1
pyridine
→
CC(C)(C)[Si](C)(C)OC[C@]12CCC(=O)C=C1CC[C@@H]1[C@@H]2CC[C@]2(C)C(=O)CC[C@@H]12
19-t-butyldimethylsiloxy-4-androstene-3,17-dione

Edukte

C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@@]43CO)[C@@H]1CCC2=O
19-Hydroxy-4-androstene-3,17-dione
CC(C)(C)[Si](C)(C)Cl
t-butyldimethylsilylchloride
c1ccncc1
pyridine

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethylformamide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturheated on a steam bath overnight
  2. 2
    workup.ADDITIONThe reaction mixture is poured onto water
  3. 3
    FiltrationThe resulting solid is filtered
  4. 4
    workup.DISSOLUTIONdissolved in methylenechloride
  5. 5
    Trocknendried over magnesium sulfate
  6. 6
    Sonstigethe solvent removed
  7. 7
    SonstigeThe residue is crystallized from an acetone-hexane solution

Vorschrift

19-Hydroxy-4-androstene-3,17-dione, t-butyldimethylsilylchloride and pyridine are mixed in dry dimethylformamide and heated on a steam bath overnight. The reaction mixture is poured onto water and stirred well for 15 minutes. The resulting solid is filtered and dissolved in methylenechloride, dried over magnesium sulfate and the solvent removed. The residue is crystallized from an acetone-hexane solution to yield 19-t-butyldimethylsiloxy-4-androstene-3,17-dione.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04087524uspto-grants-1978_05