1,3-Dimethyl-2-imidazolidinone → 5-Methoxy-3-phenyl-1-tetralone

HRID 847261

Reaktionsgleichung

Reaktionsgleichung von HRID 847261
[CH:1](=O)[C:2]1[C:3]([O:8][CH3:9])=[CH:4][CH:5]=[CH:6][CH:7]=1.C(S)CCS.S1CCCCS1.[Li]CCCC.[C:27](OC)(=[O:36])[CH:28]=[CH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.CN1CCN(C)C1=O>C(Cl)Cl>[CH3:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:2]=1[CH2:1][CH:29]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:28][C:27]2=[O:36]

Komponenten

8

Edukt 6

HCID 66611,3-Dimethyl-2-imidazolidinoneHCID 76442-Propenoic acid, 3-phenyl-, methyl esterHCID 80131,3-PropanedithiolHCID 86582-MethoxybenzaldehydeHCID 1363351,2-DithianeHCID 178418339Butyllithium

Produkt 1

HCID 122124065-Methoxy-3-phenyl-1-tetralone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

o- Anisaldehyde (20.5 g) was treated with 1,3-propanedithiol (24 ml) in the presence of BF. etherate (4 ml) and CH2Cl2 (300 ml). This dithiane derivative (4.7 g) was reacted with n-BuLi (2.5 M hexane solution) (7.3 ml), methyl cinnamate (3.4 g) and 1,3-dimethyl-2-imidazolidone (4.6 ml) affording the desired product (M+H)+ 389. Desulfurization was accomplished with Raney Nickel and EtOH, followed by hydrolysis to the desired carboxylic acid. Cyclization to the desired 5-methoxy-3-phenyl-1-tetralone was accomplished by heating with polyphosphoric acid, (M+H)+ 253.

Quellen und Nachweise

ORD-Eintrag
ord-8836dce887c547c29440b5ab9103838c
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05140040

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