Stannous Chloride → HCID 59609202, Verbindung

HRID 1509353Notizen

Reaktionsgleichung

[S:1]1[CH:5]=[CH:4][C:3]2[C:6](=O)[C:7]3[S:8][CH:9]=[CH:10][C:11]=3[C:12](=O)[C:2]1=2.[CH2:15]([CH:17]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:18][Mg]Br)[CH3:16].Cl[Sn]Cl>C1COCC1.Cl>[CH2:15]([CH:17]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:18][C:6]1[C:7]2[S:8][CH:9]=[CH:10][C:11]=2[C:12]([CH2:6][CH:3]([CH2:4][CH3:5])[CH2:2][CH2:12][CH2:11][CH3:7])=[C:2]2[S:1][CH:5]=[CH:4][C:3]=12)[CH3:16]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a suspension of benzo[1,2-b:4,5-b′]dithiophene-4,8-dione (25) (Beimling, P.; Koβmehl, G. Chem. Ber. 1986, 119, 3198) (4.9 g, 22.2 mmol) in 100 mL of THF was added 2-ethylhexyl magnesium bromide (111 mL, 1M in diethyl ether). The mixture was then heated at 60° C. for 24 h., and cooled to r.t. following by adding SnCl2 (13.47 g, 71.04 mmol) in 190 mL of 10% HCl. The mixture was heated at 60° C. for 24 h. THF was removed under reduced pressure. The residure was dissolved in ether, washed with water, sat. NaHCO3, brine and water. The organic layer was dried over MgSO4 and then concentrated. Column chromatography with hexane gave 1.2 g (13%) of desired product 26. 1H-NMR (400 MHz, CDCl3): ppm 7.46 (d, 2H, J=5.6 Hz), 7.42 (d, 2H, J=5.6 Hz), 3.18-3.06 (m, 4H), 1.97 (hep, 2H, J=6.4 Hz), 1.43-1.18 (m, 16H), 0.91-0.81 (m, 12H).

Aufarbeitung

temperaturecooled to r.t.
temperatureThe mixture was heated at 60° C. for 24 h
customTHF was removed under reduced pressure
dissolutionThe residure was dissolved in ether
washwashed with water, sat. NaHCO3, brine and water
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-72106297f42a46d294a19713264ac56a
Quelldatensatz: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09221944B2

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