Estrone → 17-Methylene-estra-1,3,5(10)-trien-3-ol

HRID 963182

Reaktionsgleichung

Reaktionsgleichung von HRID 963182
[CH3:1]C(C)([O-])C.[K+].[CH3:7][C@@:8]12[C:24](=O)[CH2:23][CH2:22][C@H:21]1[C@H:20]1[C@@H:11]([C:12]3[CH:13]=[CH:14][C:15]([OH:26])=[CH:16][C:17]=3[CH2:18][CH2:19]1)[CH2:10][CH2:9]2>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH2:1]=[C:24]1[CH2:23][CH2:22][C@H:9]2[C@H:10]3[C@H:11]([CH2:20][CH2:21][C@:8]12[CH3:7])[C:12]1[CH:13]=[CH:14][C:15]([OH:26])=[CH:16][C:17]=1[CH2:18][CH2:19]3

Komponenten

5

Edukt 2

HCID 5870EstroneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 1445855217-Methylene-estra-1,3,5(10)-trien-3-olAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74505Methyltriphenyliphosphonium bromideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of methyl triphenylphosphonium bromide (8.93 g, 25.0 mmol) in THF (120 mL) was added potassium tert-butoxide (2.69 g, 24 mmol) and stirred for 30 min at room temperature. The reaction mixture was added estrone (18, 2.70 g, 10 mmol), stirred for 19 h at room temperature. The reaction mixture was quenched with saturated aqueous NH4Cl at 0° C. and extracted with EtOAc. The combined organic layers were washed with H2O, then with saturated aqueous NaCl, and 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 (5:1→3:1, v/v) to afford 2.24 g of 19 (84% yield), m.p. 135°-136° C.

Aufarbeitung

  1. stirringstirred for 19 h at room temperature
  2. customThe reaction mixture was quenched with saturated aqueous NH4Cl at 0° C.
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with H2O
  5. dry with materialwith saturated aqueous NaCl, and dried (Na2SO4)
  6. filtrationThe desiccant was filtered
  7. customthe solvent was evaporated at reduced pressure
  8. customThe residue was purified by column chromatography (silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-d9ddb7e30d5b47c69360a74f2ffff16d
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05763432

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