反応式
[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]([Mg]Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].Cl[Sn]Cl>C1COCC1>[CH2:15]([C:6]1[C:7]2[S:8][CH:9]=[CH:10][C:11]=2[C:12]([CH2:5][CH2:4][CH2:3][CH2:2][CH2:12][CH2:11][CH2:7][CH3:6])=[C:2]2[S:1][CH:5]=[CH:4][C:3]=12)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]参加物
実験手順
To a 100 mL flask under nitrogen was added 4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophene-4,8-dione (1.1 g, 5.0 mmol) and anhydrous THF (10 mL). The mixture was heated to reflux and octylmagnesium bromide (20 mmol, 10 mL, 2.0 M in Et2O) was added dropwise. After refluxing for 2 hours more, SnCl2 solution (7.3 g in 19 mL 10% HCl) was slowly added dropwise. The mixture was kept at 60° C. for 1 hour. After cooling down, the organic phase was separated. The water phase was extracted with ether once and the organic phases were combined and dried over Na2SO4. Purification by column chromatography with hexane as eluent gave a yellow oil (780 mg, yield 37.6%). 1H NMR (CDCl3, 500 MHz) δ=7.48 (d, J=5.5 Hz, 2H), 7.47 (d, J=5.5 Hz, 2H), 3.20 (t, J=7.5 Hz, 4H), 1.75-1.88 (m, 4H), 1.43-1.54 (m, 4H), 1.21-1.42 (bs, 16H), 0.90 (t, J=7.0 Hz, 6H).
後処理
- temperatureThe mixture was heated
- temperatureto reflux
- temperatureAfter refluxing for 2 hours more
- temperatureAfter cooling down
- customthe organic phase was separated
- extractionThe water phase was extracted with ether once
- dry with materialdried over Na2SO4
- customPurification by column chromatography with hexane as eluent
出典と根拠
- ORDレコード
- ord-2daccca19c4d4c8f861443e5814d4e3e
- 出典データセット
- uspto-grants-2012_12
- 特許番号
- US08334456B2
関連ノート
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