Reaction equation
[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]Participants
Conditions
- Temperature
- 60 °C
Procedure
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).
Workup
- 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
Sources & evidence
- ORD record
- ord-72106297f42a46d294a19713264ac56a
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09221944B2
Linked notes
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