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Water → 4,8-Bis(10-phenyldecyl)-2,6-bis-trimethylstannylbenzo[1,2-b:4,5-b']dithiophene

HRID 2195099
ノート
印刷プレビュー

反応式

HRID 2195099 の反応式
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[S:26][CH:27]=[CH:28][C:24]=3[C:23]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[C:19]3[S:20][CH:21]=[CH:22][C:18]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH3:50][Sn:51](Cl)([CH3:53])[CH3:52].O>O1CCCC1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]2[C:25]3[S:26][C:27]([Sn:51]([CH3:53])([CH3:52])[CH3:50])=[CH:28][C:24]=3[C:23]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)=[C:19]3[S:20][C:21]([Sn:51]([CH3:53])([CH3:52])[CH3:50])=[CH:22][C:18]=23)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 668211144,8-Bis(10-phenyldecyl)benzo[1,2-b:4,5-b']dithiopheneHCID 178418339Butyllithium

生成物 1

HCID 866482724,8-Bis(10-phenyldecyl)-2,6-bis-trimethylstannylbenzo[1,2-b:4,5-b']dithiophene収率 70%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

実験手順

To a solution of 4,8-bis(10-phenyldecyl)benzo[1,2-b:4,5-b′]dithiophene (466 mg, 0.75 mmol) in dry tetrahydrofuran (15 mL) was added n-butyllithium (2.5 M in hexane, 0.66 mL, 1.65 mmol) at −78° C. After 1 hour, trimethyltin chloride (349 mg, 1.75 mmol) was added in one portion. The mixture was stirred at room temperature overnight, poured into water (25 mL) and extracted with ether three times. The organic layer was washed with brine and dried over anhydrous MgSO4. Upon evaporating the solvent, a pale yellow oil was obtained (500 mg, yield 70%). 1H NMR (CDCl3, 500 MHz) δ=7.49 (s, 2H), 7.27-7.32 (m, 4H), 7.17 (d, J=7.5 Hz, 6H), 3.19 (t, J=7.5 Hz, 4H), 2.59 (t, J=8.0 Hz, 4H), 1.75-1.84 (m, 4H), 1.56-1.66 (m, 4H), 1.42-1.50 (m, 4H), 1.17-1.41 (m, 20H), 0.45 (s, 18H).

後処理

  1. extractionextracted with ether three times
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. customUpon evaporating the solvent
  5. customa pale yellow oil was obtained (500 mg, yield 70%)

出典と根拠

ORDレコード
ord-af9c78a8a42142488b6d81dc6600a49f
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08334456B2

反応ノート

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