Carbon Dioxide → 2,2'-Bithiophene-5-carboxylic acid

HRID 1835469

Reaktionsgleichung

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.C([Li])CCC.[C:16](=[O:18])=[O:17].Cl>O1CCCC1.CCCCCC.C(OCC)(=O)C>[S:1]1[C:5]([C:16]([OH:18])=[O:17])=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1

Komponenten

Reaktionsbedingungen

Temperatur: -60 °C

Versuchsvorschrift

To a suspension of 2,2′-bithiophene (1.0 g) in tetrahydrofuran (10 ml) was added a solution of n-butyl lithium in n-hexane (1.54 M, 4.3 ml) at −25° C. under nitrogen atmosphere. The mixture was stirred at −60° C. for 30 minutes. To the solution dry-ice (1.0 g) was added and the mixture was stirred at ambient temperature for 30 minutes. To the resultant suspension hydrochloric acid (1N, 10 ml) and ethyl acetate were added. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether. The resulting precipitate was collected by filtration, washed with diisopropyl ether and dried to give [2,2′]bithiophenyl-5-carboxylic acid (952 mg, 75.6%).

Aufarbeitung

stirringthe mixture was stirred at ambient temperature for 30 minutes
washThe separated organic layer was washed with brine
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure
customThe residue was triturated with diisopropyl ether
filtrationThe resulting precipitate was collected by filtration
washwashed with diisopropyl ether
customdried

Quellen und Nachweise

ORD-Eintrag: ord-1818d00f6c8f4f73891ffaf279776cd8
Quelldatensatz: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06770667B1

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