Dimethylformamide → 9-(4-Hydroxy-phenyl)-10-methoxymethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-ol

HRID 418970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418970
C[O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH:13]([CH2:17][O:18][CH3:19])[CH:12]([C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.C([S-])C.[Na+].CN(C=O)C>C(OCC)(=O)C>[OH:26][C:23]1[CH:24]=[CH:25][C:20]([CH:12]2[CH:13]([CH2:17][O:18][CH3:19])[C:14]3[CH:15]=[CH:16][C:3]([OH:2])=[CH:4][C:5]=3[CH:6]3[CH:11]2[CH2:10][CH2:9][CH2:8][CH2:7]3)=[CH:21][CH:22]=1

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 4459711Sodium ethanethiolateHCID 666519026-Methoxy-9-methoxymethyl-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

Produkt 1

HCID 666519829-(4-Hydroxy-phenyl)-10-methoxymethyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-olAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Combine 6-methoxy-9-methoxymethyl-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene (0.050 g, 0.14 mmol), sodium ethanethiolate (0.037 g, 0.44 mmol), and DMF (4 mL), and reflux under nitrogen atmosphere. After 18 hours, cool the reaction to room temperature and add ethyl acetate, wash with sat ammonium chloride solution (aq), then brine several times. Concentrate, and purify using reverse phase chromatography (5% to 95% 0.001% TFA buffer in acetonitrile/water) to yield the titled compound (0.015 g, 33%) as a white solid. TLC Rf=0.27 in 3:1 hexanes:ethyl acetate. 1H NMR (d-methanol): 7.42 (d, 1H, J=8.4 Hz), 7.13 (d, 2H, J=8.4 Hz), 6.84 (s, 1H), 6.79 (d, 2H, J=8.4 Hz), 6.65 (dd, 1H, J=7.9, 1.8 Hz), 3.70 (d, 1H, J=7.0 Hz), 3.35 (m, 3H), 3.17 (s, 3H), 3.07 (m, 1H), 2.48 (d, 1H, J=14.1 Hz), 1.87 (m, 1H), 1.64 (m, 2H), 1.41 (m, 2H), 1.16 (m, 3H).

Aufarbeitung

  1. temperaturecool
  2. customthe reaction to room temperature
  3. washwash with sat ammonium chloride solution (aq)
  4. concentrationConcentrate
  5. custompurify

Quellen und Nachweise

ORD-Eintrag
ord-ba9f58d2808e4da498f3448912bbe0b5
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093302B2

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