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2-Thiophenecarboxaldehyde, 5-iodo- → HCID 86678076、化合物

HRID 2369760
ノート
印刷プレビュー

反応式

HRID 2369760 の反応式
[C:1]([C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9]([C:16]#[CH:17])=[CH:10][CH:11]=3)[C:6]([CH2:22][CH2:23][CH2:24][CH3:25])([CH2:18][CH2:19][CH2:20][CH3:21])[C:5]=2[CH:4]=1)#[CH:2].I[C:27]1[S:31][C:30]([CH:32]=[O:33])=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.CCN(CC)CC.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:22]([C:6]1([CH2:18][CH2:19][CH2:20][CH3:21])[C:7]2[CH:8]=[C:9]([C:16]#[C:17][C:27]3[S:31][C:30]([CH:32]=[O:33])=[CH:29][CH:28]=3)[CH:10]=[CH:11][C:12]=2[C:13]2[C:5]1=[CH:4][C:3]([C:1]#[C:2][C:27]1[S:31][C:30]([CH:32]=[O:33])=[CH:29][CH:28]=1)=[CH:15][CH:14]=2)[CH2:23][CH2:24][CH3:25]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 30143612-Thiophenecarboxaldehyde, 5-iodo-HCID 86678075HCID 86678075、化合物

生成物 1

HCID 86678076HCID 86678076、化合物収率 97.4%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒
HCID 22504574
Toluene triethylamine
溶媒

反応条件

温度
40 °C

実験手順

Air was removed from a solution of 2,7-diethynyl-9,9-dibutyl-9H-fluorene (0.150 g, 0.460 mmol) and 5-iodothiophene-2-carboxaldehyde (Wu, L.-H.; Chu, C.-S.; Janarthanan, N.; Hsu, C.-S. J. Polym. Res. 2000, 7, 125-134) (0.251 g, 1.06 mmol) in 6.5 mL of toluene/Et3N (4/1) by blowing argon for 20 min. Then CuI (7.0 mg, 0.0037 mmol) and Pd(PPh3)2Cl2 (27 mg, 0.0039 mmol) were added, and deaeration was continued for 10 min. Thereafter the mixture was stirred at 40° C. for 16 h. The solvent was removed under reduced pressure, and the crude product was purified by column chromatography (heptane/CH2Cl2 50:50 then 40:60) to yield 245 mg (97%) of 5,5′-(9,9-dibutyl-9H-fluorene-2,7-diyldi-2,1-ethynediyl)bis-2-thiophenecarboxaldehyde; 1H NMR (300.13 MHz, CDCl3) δ 9.80 (s, 2H), 7.61 and 7.26 (AX, JAX=3.9 Hz, 4H), 7.62 (d, J=8.5 Hz, 2H), 7.47 (d, J=8.5 Hz, 2H), 7.45 (s, 2H), 1.93 (m, 4H), 1.02 (m, 4H), 0.60 (t, J=7.3 Hz, 6H), 0.51 (m, 4H); 13C NMR (75.46 MHz, CDCl3) δ 182.4, 151.4, 143.9, 141.4, 136.1, 133.0, 132.5, 131.0, 126.0, 120.9, 120.4, 98.9, 82.6, 55.3, 40.1, 25.9, 23.0, 13.8; HRMS (ESI) calcd for C35H30O2S2 (M+·) m/z 546.16872. found 546.1687.

後処理

  1. customfor 20 min
  2. customThe solvent was removed under reduced pressure
  3. customthe crude product was purified by column chromatography (heptane/CH2Cl2 50:50

出典と根拠

ORDレコード
ord-bafe06b25218426e81261ae1df4244e6
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08709747B2

反応ノート

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