Phenethylthiophenol → HCID 178420258, Verbindung

HRID 1895566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1895566
O[C@H:2]1[C:23]2[C:14](=[CH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:13](O)[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]3)=[CH:4][C:3]1=2.[CH2:25]([C:33]1C=CC=C[C:34]=1[SH:39])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>[I-].[Zn+2].[I-].C(Cl)Cl>[CH2:25]([CH2:33][CH2:34][S:39][C@H:2]1[C:23]2[C:14](=[CH:15][C:16]3[C:21]([CH:22]=2)=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:13]([S:39][CH2:34][CH2:33][CH2:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:12]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[CH:9]3)=[CH:4][C:3]1=2)[CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Komponenten

5

Edukt 2

HCID 67226359PhenethylthiophenolHCID 178521537HCID 178521537, Verbindung

Produkt 1

HCID 178420258HCID 178420258, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9883512zinc(II)iodideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of trans-6,13-dihydroxy-6,13-dihydropentacene (1.0 g, 3.20 mmol) and zinc iodide (1.02 g, 3.20 mmol) were added successively dry CH2Cl2 (100 mL) and phenethylthiophenol (0.77 g, 7.03 mmol) at RT under an argon atmosphere. The resulting mixture was stirred at RT for 2 h, and then quenched with H2O. The mixture was extracted with CH2Cl2, and the organic layer was washed with brine and dried over anhyd. Na2SO4. After evaporation of solvents, the residue was purified by column chromatography on silica gel eluted with n-hexanes-CH2Cl2 (2:1) to give product as white solids in 71% yield (1.13 g). 1H NMR (500 MHz, CDCl3): δ 7.80 (m, 4H), 7.70 (s, 4H), 7.46 (m, 4H), 7.29 (t, 4H, J=7.56 Hz), 7.20 (m, 6H), 5.24 (s, 2H), 2.90 (s, 8H). LDI-MS m/z: 552 [M+], 416 [M+-SCH2CH2C6H5], 280 [M+-2(SCH2CH2C6H5)].

Aufarbeitung

  1. customquenched with H2O
  2. extractionThe mixture was extracted with CH2Cl2
  3. washthe organic layer was washed with brine
  4. customdried over anhyd
  5. customAfter evaporation of solvents
  6. customthe residue was purified by column chromatography on silica gel
  7. washeluted with n-hexanes-CH2Cl2 (2:1)
  8. customto give product as white solids in 71% yield (1.13 g)

Quellen und Nachweise

ORD-Eintrag
ord-75465c89ac2d436ea923bb5810711ca3
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513466B2

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