Reaktionsgleichung
BrC1C=C2C(=CC=1OCCCCC)C(C)(C)CCC2(C)C.C([Li])(C)(C)C.C(=O)=O.[CH2:30]([O:35][C:36]1[C:37]([C:50]([OH:52])=[O:51])=[CH:38][C:39]2[C:40]([CH3:49])([CH3:48])[CH2:41][CH2:42][C:43]([CH3:47])([CH3:46])[C:44]=2[CH:45]=1)[CH2:31][CH2:32][CH2:33][CH3:34].O[C:54]1[CH:69]=[CH:68][C:57]([C:58]([O:60][CH2:61][C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[O:59])=[CH:56][N:55]=1>>[CH2:30]([O:35][C:36]1[C:37]([C:50]([O:52][C:54]2[CH:69]=[CH:68][C:57]([C:58]([O:60][CH2:61][C:62]3[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=3)=[O:59])=[CH:56][N:55]=2)=[O:51])=[CH:38][C:39]2[C:40]([CH3:49])([CH3:48])[CH2:41][CH2:42][C:43]([CH3:46])([CH3:47])[C:44]=2[CH:45]=1)[CH2:31][CH2:32][CH2:33][CH3:34]Komponenten
6
Edukt 5
Produkt 1
Versuchsvorschrift
In analogy to Example 1, by metallating 6-bromo-7-pentoxy-1,1,4,4-tetramethyl-1,2,3,4-tetrahydro-naphthalene with tert.butyl-lithium and reacting with carbon dioxide gas there was prepared 3-pentoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid (m.p. 67°-68° C., from hexane). Reaction of this acid with benzyl 6-hydroxy-nicotinate gave benzyl 6-(3-pentoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-carbonyloxy)-nicotinate as a colorless oil. Subsequent hydrogenation yielded the desired end product 6-(3-pentoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl-carbonyloxy)-nicotinic acid in white crystals, m.p. 132°-133° C. (from diethyl ether/hexane).
Quellen und Nachweise
- ORD-Eintrag
- ord-34b88de89a834c5b93af8ffabf69f38c
- Quelldatensatz
- uspto-grants-1998_03
- Patentnummer
- US05726191
Verknüpfte Notizen
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