Triphenylphosphine → 11-Bromoundecylmaleimide pentacene

HRID 500287노트

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HRID 500287 반응식
[CH:1]1[C:22]2[C:5](=[CH:6][C:7]3[C:20]([CH:21]=2)=[CH:19][C:18]2[C:9](=[CH:10][C:11]4[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=4)[CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[C:23]1(=[O:29])[NH:27][C:26](=[O:28])[CH:25]=[CH:24]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[Br:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][C:24]1[C:23]([NH:27][C:26](=[O:28])[CH:25]=1)=[O:29].[CH:4]1[C:5]2[C:22](=[CH:21][C:20]3[C:7]([CH:6]=2)=[CH:8][C:9]2[C:18](=[CH:17][C:16]4[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:19]=3)[CH:1]=[CH:2][CH:3]=1.[Br:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][N:27]1[C:26](=[O:28])[CH:25]=[CH:24][C:23]1=[O:29].[CH:4]1[C:5]2[C:22](=[CH:21][C:20]3[C:7]([CH:6]=2)=[CH:8][C:9]2[C:18](=[CH:17][C:16]4[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH:19]=3)[CH:1]=[CH:2][CH:3]=1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 7416311-Bromo-1-undecanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86643198Pentacene maleimide

생성물 2

HCID 8664775211-Bromoundecylmaleimide pentaceneHCID 86647754N-(11-bromoundecyl) maleimide pentacene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Pentacene-maleimide adduct (5c) (375 mg, 1 mmole) are added to a solution of triphenyl phosphine (393 mg, 1.5 mmole) and 11-bromo-1-undecanol (375 mg, 1.5 mmole) in 40 mL of anhydrous tetrahydrofuran. To this mixture a solution of diisopropyl azodicarboxylate (300 mg, 1.5 mmole) in 10 mL of anhydrous THF is added dropwise under a stream of nitrogen. After completion of the addition, the solution is stirred at room temperature for 18 hours. The solvent is evaporated under reduced pressure and the residue is titrated with diethyl ether and the precipitate is filtered, washed with 1:1 ether-hexane and dried. Crystallization from benzene affords the pure sample of 11-bromoundecylmaleimide-pentacene adduct 5d.

후처리

  1. additionAfter completion of the addition
  2. customThe solvent is evaporated under reduced pressure
  3. filtrationthe precipitate is filtered
  4. washwashed with 1:1 ether-hexane
  5. customdried
  6. customCrystallization from benzene

출처 및 근거

ORD 기록
ord-8ca79133d16f4ad49136e6255d18ca23
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07771695B2

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