Sodium hydride → HCID 21967810, Verbindung

HRID 1003185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1003185
C([O:4][C:5]1[C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:27])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1)(=O)C.[H-].[Na+]>C1COCC1.CO>[OH:4][C:5]1[C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][C:20]2[C@@H:19]3[C@H:10]([C@H:11]4[C@@:15]([CH2:17][CH2:18]3)([CH3:16])[C:14](=[O:27])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C:7]=2[CH:6]=1

Komponenten

5

Edukt 2

HCID 24758Sodium hydrideHCID 21967809HCID 21967809, Verbindung

Produkt 1

HCID 21967810HCID 21967810, VerbindungAusbeute 87,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 3-acetoxyestra-1,3,5(10)-trien-17-one-2-carboxylate (63, 0.746 g, 2.0 mmol) in THF (10 mL) and MeOH (15 mL) was added sodium hydride (0.240 g of a mineral oil dispersion, 60%, 6.0 mmol) at 0° C. The reaction mixture was stirred for 30 min, and quenched with saturated aqueous NH4Cl at 0° C., and extracted with EtOAc. The combined organic layers were washed with H2O, saturated aqueous NaCl, and then dried (Na2SO4). The desiccant was filtered and the solvent was evaporated at reduced pressure. The residue was purified by column chromatography (silica gel) using n-hexane:EtOAc (3:1, v/v) to afford 0.572 g of 64 (87% yield) mp: 178-179° C.

Aufarbeitung

  1. customquenched with saturated aqueous NH4Cl at 0° C.
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O, saturated aqueous NaCl
  4. dry with materialdried (Na2SO4)
  5. filtrationThe desiccant was filtered
  6. customthe solvent was evaporated at reduced pressure
  7. customThe residue was purified by column chromatography (silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-6a46bd4cca574b318f9412302e6b827c
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046186

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