반응 #2507810

ord-765367a56c704df5bf811e861c0317ca

반응 방정식

CC(C)OC(=O)N=NC(=O)OC(C)C
diisopropyl azodicarboxylate
O=C1C=CC(=O)N1.c1ccc2cc3cc4cc5ccccc5cc4cc3cc2c1
Pentacene maleimide
O=C1C=CC(=O)N1.c1ccc2cc3cc4cc5ccccc5cc4cc3cc2c1
Pentacene Maleimide
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenyl phosphine
OCCCCCCCCCCCBr
11-bromo-1-undecanol
O=C1C=CC(=O)N1CCCCCCCCCCCBr.c1ccc2cc3cc4cc5ccccc5cc4cc3cc2c1
5d
O=C1C=CC(=O)N1CCCCCCCCCCCBr.c1ccc2cc3cc4cc5ccccc5cc4cc3cc2c1
N-(11-bromoundecyl) maleimide pentacene
O=C1C=C(CCCCCCCCCCCBr)C(=O)N1.c1ccc2cc3cc4cc5ccccc5cc4cc3cc2c1
11-bromoundecylmaleimide pentacene

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    workup.ADDITIONAfter completion of the addition
  2. 2
    기타The solvent is evaporated under reduced pressure
  3. 3
    여과the precipitate is filtered
  4. 4
    세척washed with 1:1 ether-hexane
  5. 5
    기타dried
  6. 6
    기타Crystallization from benzene

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07955585B2uspto-grants-2011_06