Diethyl Ether → 3-[3-Methoxy-9-(4-methoxy-phenyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-2-yl]-acrylic acid ethyl ester

HRID 418940Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418940
[CH3:1][O:2][C:3]1[C:4](C=O)=[CH:5][C:6]2[CH2:7][CH:8]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[CH:9]3[CH:14]([C:15]=2[CH:16]=1)[CH2:13][CH2:12][CH2:11][CH2:10]3.[C:27]([C:32]1C=CC=C[C:33]=1P(=C)(C1C=CC=CC=1)C1C=CC=CC=1)([O:29][CH2:30][CH3:31])=[O:28].C(OCC)C>C1(C)C=CC=CC=1>[CH2:30]([O:29][C:27](=[O:28])[CH:32]=[CH:33][C:4]1[C:3]([O:2][CH3:1])=[CH:16][C:15]2[CH:14]3[CH:9]([CH2:10][CH2:11][CH2:12][CH2:13]3)[CH:8]([C:17]3[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=3)[CH2:7][C:6]=2[CH:5]=1)[CH3:31]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 53442634Carbethoxy-methylene triphenylphosphoraneHCID 723094303-Methoxy-9-(4-methoxy-phenyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthrene-2-carbaldehyde

Produkt 1

HCID 666521583-[3-Methoxy-9-(4-methoxy-phenyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-2-yl]-acrylic acid ethyl esterAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Combine 3-Methoxy-9-(4-methoxy-phenyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthrene-2-carbaldehyde (1.77 g, 5.13 mmol), carboethoxy-methylene triphenylphosphorane (03.19 g, 9.03 mmol) in toluene (53 ml) and reflux 15 hours. Remove solvent in vacuo, slurry with diethyl ether and chromatograph the residue from the concentrated filtrate on silica gel with 20% ethyl acetate/hexanes, then 25% ethyl acetate/hexanes to yield the titled compound (1.61 g, 76%). MS m/z 421(M+1).

Quellen und Nachweise

ORD-Eintrag
ord-43ef1dcf660e406a94c1211f19f1bfa0
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093302B2

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