Hexane → 5-Trimethylstannyl-4,4'-didodecyl-2,2'-bithiophene

HRID 1257981ノート

反応式

HRID 1257981 の反応式
Br[C:2]1[S:6][C:5]([C:7]2[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:11]=2)=[CH:4][C:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].C([Li])CCC.CCCCCC.[CH3:47][Sn:48](Cl)([CH3:50])[CH3:49]>C1COCC1.C(OCC)C.O>[CH3:47][Sn:48]([CH3:50])([CH3:49])[C:2]1[S:6][C:5]([C:7]2[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:11]=2)=[CH:4][C:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

参加物

8

反応物 4

HCID 8058HexaneHCID 14016Trimethyltin chlorideHCID 671208205-Bromo-4,4'-didodecyl-2,2'-bithiopheneHCID 178418339Butyllithium

生成物 1

HCID 575726935-Trimethylstannyl-4,4'-didodecyl-2,2'-bithiophene収率 90%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of 5-bromo-4,4′-didodecyl-2,2′-bithiophene (29A, 100 mg, 0.172 mmol) in 4.0 mL of THF was added dropwise a solution of n-butyllithium in hexane (0.076 mL, 2.5 M, 0.189 mmol) at −78° C. The solution was stirred at −78° C. for 1 hour and a solution of trimethyltin chloride in THF (0.20 mL, 1.0 M, 0.20 mmol) was added in one portion. The solution was warmed to room temperature and 10.0 mL of water and 10.0 mL of diethylether were added. The organic layer was separated and washed twice with 20 mL of water and dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo to yield 5-trimethylstannyl-4,4′-didodecyl-2,2′-bithiophene (29, 0.103 g, 90% yield) as a yellow oil. 1H NMR (CDCl3): δ 0.84-1.64 (m, 46H), 2.58 (m, 4H), 6.77 (s, 1H), 6.99 (s, 1H), 7.13 (s, 1H).

後処理

  1. temperatureThe solution was warmed to room temperature
  2. customThe organic layer was separated
  3. washwashed twice with 20 mL of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-cb0ead2b64da435eb05658c051c743c5
出典データセット
uspto-grants-2013_06
特許番号
USRE044304E1

反応ノート

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