Pyridine → Estra-1,3,5(10),7,16-pentaen-3-yl acetate

HRID 1107200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1107200
C=[CH:2][C@@H:3]([CH3:24])[C@@H:4]1[C@:21]2(C)[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2(C)[C:11](=CC(=O)[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.N1C=CC=CC=1.[C:31]([O:34]C(=O)C)(=[O:33])[CH3:32]>C(OCC)(=O)C>[C:31]([O:34][C:19]1[CH:20]=[CH:21][C:7]2[C@@H:6]3[C:11]([C@H:16]4[C@@:3]([CH2:4][CH2:5]3)([CH3:24])[CH:2]=[CH:14][CH2:15]4)=[CH:10][CH2:9][C:8]=2[CH:18]=1)(=[O:33])[CH3:32]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 1542966021-methylene-20(R)-methylpregn-4-en-3-one

Produkt 1

HCID 68410585Estra-1,3,5(10),7,16-pentaen-3-yl acetateAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of estra-1,3,5(10),7,16-pentaen-3-ol (5, 192.1 mg, 0.7612 mmol) in anh. pyridine (2.6 ml, 32 mmol) and acetic anhydride (0.36 ml, 3.8 mmol) was stirred 6 h, after which 30 ml of ethyl acetate were added. The mixture was washed with three 10 ml portions of 1 N hydrochloric acid+10 ml of saturated sodium bicarbonate+10 ml of brine, dried over magnesium sulfate, and filtered through diatomaceous earth. See Example 15. The residue was washed with 10 ml of ethyl acetate and the combined filtrates were concentrated under reduced pressure. Preparative TLC (5% ethyl acetate/hexanes on silica gel GF, 1000μ thickness) and recrystallization from aqueous ethanol gave fine white needles (78.6 mg, 0.267 mmol, 35%), m.p. 77-80° C. TLC (4% ethyl acetate/hexanes on silica gel) showed 2 spots at Rf 0.21 and 0.24.

Aufarbeitung

  1. washThe mixture was washed with three 10 ml portions of 1 N hydrochloric acid+10 ml of saturated sodium bicarbonate+10 ml of brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered through diatomaceous earth
  4. washThe residue was washed with 10 ml of ethyl acetate
  5. concentrationthe combined filtrates were concentrated under reduced pressure
  6. customPreparative TLC (5% ethyl acetate/hexanes on silica gel GF, 1000μ thickness) and recrystallization from aqueous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4ae38e715a1140fd92d82d8d5c504c0f
Quelldatensatz
uspto-grants-2000_05
Patentnummer
US06057439

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