Dimethylformamide → 4-(Octynyl)-3-thiophenecarboxaldehyde

HRID 569494

Reaktionsgleichung

Reaktionsgleichung von HRID 569494
Br[C:2]1[C:6]([C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[CH:5][S:4][CH:3]=1.C([Li])CCC.CCCCCC.CN(C)[CH:28]=[O:29]>O1CCCC1.CCOCC>[C:7]([C:6]1[C:2]([CH:28]=[O:29])=[CH:3][S:4][CH:5]=1)#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 201471773-Bromo-4-(1-octynyl)thiopheneHCID 178418339Butyllithium

Produkt 1

HCID 201471584-(Octynyl)-3-thiophenecarboxaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-Bromo-4-(1-octynyl)thiophene (2.0 g, 7.38 mM) was dissolved in dry tetrahydrofuran under argon. Butyl lithium (2.85 ml of a 2.6M hexane solution) was added keeping the temperature at -20° C. After 30 min at this temperature, N,N-dimethl formamide (2 ml) was added and the mixture allowed to attain room temperature overnight. Hydrolysis and extraction with ether yielded a yellow oil (1.70 g) which was purified by chromatography on silica eluting with chloroform/hexane (1:1). This gave 550 mg (34%) of the title compound as a yellow oil. νmax (film) 3100, 2225, 1680, 880, 760, 670; δ(CDCl3) 0.93(3H, t, J=6 Hz), 1.3(8H, m), 2.2(2H, t, 6 Hz), 7.25(1H, s), 7.67(1H, s), 9.93(1H, s).

Aufarbeitung

  1. customat -20° C

Quellen und Nachweise

ORD-Eintrag
ord-41de8c278ae54a56aa5d2440b9503ed9
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04732901

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