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2-Thiophenecarboxaldehyde, 5-iodo- → HCID 86678079、化合物

HRID 2369764
ノート
印刷プレビュー

反応式

HRID 2369764 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]([CH2:28][CH2:29][O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][O:36][CH3:37])([CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[C:5]=2[CH:4]=1)#[CH:2].I[C:39]1[S:43][C:42]([CH:44]=[O:45])=[CH:41][CH:40]=1>C1(C)C=CC=CC=1.CCN(CC)CC.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.[Cu]I>[CH3:37][O:36][CH2:35][CH2:34][O:33][CH2:32][CH2:31][O:30][CH2:29][CH2:28][C:6]1([CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH3:27])[C:7]2[CH:8]=[C:9]([C:16]#[C:17][C:39]3[S:43][C:42]([CH:44]=[O:45])=[CH:41][CH:40]=3)[CH:10]=[CH:11][C:12]=2[C:13]2[C:5]1=[CH:4][C:3]([C:1]#[C:2][C:39]1[S:43][C:42]([CH:44]=[O:45])=[CH:41][CH:40]=1)=[CH:15][CH:14]=2
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

7

反応物 2

HCID 30143612-Thiophenecarboxaldehyde, 5-iodo-HCID 86678080HCID 86678080、化合物

生成物 1

HCID 86678079HCID 86678079、化合物収率 81.3%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒
HCID 1140
Toluene
溶媒
HCID 8471Triethylamine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-bis[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-9H-fluorene (0.120 g, 0.237 mmol) in 8.2 mL of toluene and 1.8 mL of Et3N by blowing argon for 20 min. Then Pd(PPh3)2Cl2 (10 mg, 6 mol %) and CuI (2.7 mg, 6 mol %), and 5-iodothiophene-2-carboxaldehyde (0.135 g, 0.568 mmol) were added, and deaeration was continued for 15 min. Thereafter the mixture was stirred at 40° C. for 17 h. After completion of the reaction, reaction mixture was filtered and evaporated to dryness. The crude product was purified by column chromatography on silica gel (CH2Cl2/AcOEt 60:40 then AcOEt) to yield 0.140 g (81%) of 5,5′-[9,9-bis[2-[2-(2-methoxyethoxy)ethoxy]ethyl]-9H-fluorene-2,7-diyldi-2,1-ethynediyl]bis-2-thiophenecarboxaldehyde, mp 84° C.; 1H NMR (CDCl3) δ 2.43 (t, 4H, J=7.5 Hz), 2.79 (t, 4H, J=7.2 Hz), 3.21 (m, 4H), 3.33 (s, 6H), 3.39 (m, 4H), 3.54-3.46 (m, 8H), 7.37 (d, 2H, J=3.9 Hz), 7.57 (dd, 2H, J=1.5 Hz, J=7.1 Hz), 7.62 (d, 2H, J=1.2 Hz), 7.71 (d, 2H, J=7.1 Hz), 7.72 (d, 2H, J=3.9 Hz), 9.90 (s, 2H); 13C NMR (CDCl3) δ 39.6, 51.6, 59.0, 66.8, 70.1, 70.4, 70.5, 71.8, 83.0, 98.5, 120.5, 121.2, 126.6, 131.3, 132.6, 132.8, 136.2, 140.7, 143.9, 149.7, 182.5. HRMS (ESI) calcd for C41H42O8NaS2 [(M+Na)+] m/z 749.2219. found 749.2226. Anal. Calcd for C41H42O8S2 (726.90): C, 67.75; H, 5.82; S, 8.82. Found: C, 67.86; H, 5.82; S, 8.63.

後処理

  1. customfor 20 min
  2. customAfter completion of the reaction, reaction mixture
  3. filtrationwas filtered
  4. customevaporated to dryness
  5. customThe crude product was purified by column chromatography on silica gel (CH2Cl2/AcOEt 60:40

出典と根拠

ORDレコード
ord-e48423adaf6c42a8ab5462eccf184b41
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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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート