4H,5H,6H-cyclopenta(b)thiophen-6-one → HCID 19784313, Verbindung

HRID 256888

Reaktionsgleichung

Reaktionsgleichung von HRID 256888
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[O:12]CCO1.C([Li])(C)(C)C.[Li]C1C=CC=CC=1C1OCCO1.[S:30]1[CH:34]=[CH:33][C:32]2[CH2:35][CH2:36][C:37](=O)[C:31]1=2>>[S:30]1[CH:34]=[CH:33][C:32]2[CH2:35][CH:36]=[C:37]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[CH:8]=[O:12])[C:31]1=2

Komponenten

5

Edukt 4

HCID 3156144H,5H,6H-cyclopenta(b)thiophen-6-oneHCID 5535342-(2-Bromophenyl)-1,3-dioxolaneHCID 178418306HCID 178418306, VerbindungHCID 178506679HCID 178506679, Verbindung

Produkt 1

HCID 19784313HCID 19784313, Verbindung

Versuchsvorschrift

This scheme can be summarized as follows: 2-(2-bromophenyl)-1,3-dioxolane (A) is treated with 2 equivalents of tert-butyl lithium to effect halogen-methyl exchange. The 2-(2-lithiophenyl)-1,3-dioxolane (B) is then reacted in situ with 4,5-dihydro-6H-cyclopenta[b]thiophen-6-one. After aqueous acid workup, 2-(4H-cyclopenta[b]thiophen-6-yl)benzaldehyde (C) is isolated by flash chromatography. This is treated with a Grignard reagent (R4MgBr) to provide the 6-[2-(1-hydroxyalkyl)phenyl]-4H-cyclopenta[b]thiophene (D) which is subsequently oxidized to the 6-[2-(alkylcarbonyl)phenyl]-4H-cyclopenta[b]thiophene (E). Reductive amination of E should then provide compounds of structure III.

Quellen und Nachweise

ORD-Eintrag
ord-2ff8451779e74b99b470180da2033a28
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05260309

Verknüpfte Notizen

Wird geladen…