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2-Thiophenecarboxaldehyde, 5-iodo- → HCID 86678079, 화합물

HRID 2369764
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HRID 2369764 반응식
[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
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참가 물질

7

반응물 2

HCID 30143612-Thiophenecarboxaldehyde, 5-iodo-HCID 86678080HCID 86678080, 화합물

생성물 1

HCID 86678079HCID 86678079, 화합물수율 81.3%

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매
HCID 1140
Toluene
용매
HCID 8471Triethylamine용매

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e48423adaf6c42a8ab5462eccf184b41
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08709747B2

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