Sodium Iodide → 3-Methoxy-17-trimethylsilyloxy-estra-1,3,5(10),16-tetraene

HRID 373040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 373040
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C:12](=[O:21])[CH2:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1.C(N(CC)CC)C.[CH3:29][Si:30]([CH3:33])([CH3:32])Cl.[Na+].[I-]>C(#N)C>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][CH2:16]3)([CH3:14])[C:12]([O:21][Si:30]([CH3:33])([CH3:32])[CH3:29])=[CH:11][CH2:10]4)[CH2:7][CH2:6][C:5]=2[CH:4]=1

Komponenten

6

Edukt 4

HCID 5238Sodium Iodide3×HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 92895(+)-Estrone 3-methyl ether

Produkt 1

HCID 155961703-Methoxy-17-trimethylsilyloxy-estra-1,3,5(10),16-tetraene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

20.3 g (72 mmol) of 3-methoxy-estra-1,3,5(10)-trien-17-one is suspended with exclusion of moisture in 80 ml of acetonitrile (P2O5 and molecular sieve dried) and mixed with 17.4 ml of triethylamine (125 mmol, dried on KOH) as well as with 12.24 ml of trimethylchlorosilane (96 mmol) at an inner temperature of 35° C. Then, an NaI solution, which contains 15 g of NaI (96 mmol) in 100 ml of acetonitrile (NaI dried at 140° C. in a vacuum), is instilled in this suspension, so that the reaction temperature is kept at 35° C. without external heating. The reaction performed under nitrogen is performed with vigorous stirring. It is seen that after the addition has been completed, the amount of undissolved initial product becomes smaller. Later, the crystals completely disappeared. After 1.5 hours, the silyl enol ether begins to crystallize. After 4 hours, the crystal suspension is stirred in ice water, to which some triethylamine was added. Then, it is fritted, rewashed with water, sucked dry and the substance dried on P2O5 in a vacuum. 25.4 g of silyl enol ether, which can be recrystallized from hexane or methanol, is obtained.

Aufarbeitung

  1. customdried at 140° C. in a vacuum),
  2. customis kept at 35° C. without external heating
  3. additionafter the addition
  4. customto crystallize
  5. waitAfter 4 hours
  6. additionwas added
  7. customsucked dry
  8. customthe substance dried on P2O5 in a vacuum
  9. custom25.4 g of silyl enol ether, which can be recrystallized from hexane or methanol
  10. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-b4e2c44b66f547a6a340bdb657107bb6
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05162312

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