4,5,6,7-Tetrahydro-4-oxothionaphthene → 4,5,5a,6-tetrahydro-7H-indeno[5,4-b]thiophen-7-one

HRID 1969501Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969501
S1C2CCCC(=[O:10])C=2C=C1.[Li]C1C=CC=CC=1.C1([C:24]2[CH:35]=[C:34]3[CH:26]([CH2:27][CH2:28][C:29]4[S:30][CH:31]=[CH:32][C:33]=43)[CH:25]=2)C=CC=CC=1.C1(C2CC3C4C=CSC=4CCC=3C=2)C=CC=CC=1>CCOCC>[CH:32]1[C:33]2[C:34]3[CH:26]([CH2:25][C:24](=[O:10])[CH:35]=3)[CH2:27][CH2:28][C:29]=2[S:30][CH:31]=1

Komponenten

6

Edukt 4

HCID 834184,5,6,7-Tetrahydro-4-oxothionaphtheneHCID 58554848HCID 58554848, VerbindungHCID 67998171HCID 67998171, VerbindungHCID 178506676HCID 178506676, Verbindung

Produkt 1

HCID 585548444,5,5a,6-tetrahydro-7H-indeno[5,4-b]thiophen-7-oneAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

6,7-dihydro-1-benzothiophen-4(5H)-one was obtained with an overall yield of 43% via the acylation of thiophene by succinic anhydride followed by reduction of the ketone formed and by the cyclisation of 4-(2-thienyl)butanoic acid in the presence of the laton's reagent. Next, 4,5,5a,6-tetrahydro-7H-indeno[5,4-b]thiophen-7-one was synthesised from 6,7-dihydro-1-benzothiophen-4(5H)-one with an overall yield of 30%. The latter product was further reacted with one equivalent of PhLi in ether followed by acidification of the reaction medium to give a mixture of 7-phenyl-5,5a-dihydro-4H-indeno[5,4-b]thiophene and 7-phenyl-5,8-dihydro-4H-indeno[5,4-b]thiophene as shown in the scheme below

Aufarbeitung

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Quellen und Nachweise

ORD-Eintrag
ord-43c060e797eb4b1991f13855bee3c4e7
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426613B2

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