Benzene → 4-Methoxy-6-methylenandrost-4-ene-3,17-dione

HRID 620679Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 620679
[OH:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[C:4](=[CH2:23])[CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22].[CH:24]1C=CC=CC=1.IC>>[CH3:24][O:1][C:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C:3]=1[C:4](=[CH2:23])[CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C:10]2=[O:22]

Komponenten

4

Edukt 3

HCID 241BenzeneHCID 6328Methyl iodideHCID 186318864-Hydroxy-6-methylenandrost-4-ene-3,17-dione

Produkt 1

HCID 186318914-Methoxy-6-methylenandrost-4-ene-3,17-dioneAusbeute 75,2 %

Versuchsvorschrift

To a solution of 4-hydroxy-6-methylenandrost-4-ene-3,17-dione (0.315 g, 1 mmole) in benzene (10 ml) potassium tert-butoxide (0.224 g, 2 mmole) is added and the mixture heated to reflux for 30 minutes. After cooling, iodomethane (0.710 g, 5 mmole) is added and the mixture boiled for a further 2 hours. Then the organic solution is washed with water, dried and evaporated in vacuum. Flash column chromatography of the residue on silica gel using n-hexane/ethyl acetate 60:40 affords 0.247 g (75% yield) of the title compound, m.p. 196°-198° C.

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureto reflux for 30 minutes
  3. temperatureAfter cooling
  4. washThen the organic solution is washed with water
  5. customdried
  6. customevaporated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2a4c1910f78941c1b51724d1e4461bca
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04822528

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