2-Methylbenzenesulfonic acid → Dithiophenylacetic Acid, 2-(2-pyridinyl)ethyl Ester

HRID 24297

Reaktionsgleichung

Reaktionsgleichung von HRID 24297
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[C:7]([OH:9])=[O:8].[CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)=[CH2:16].C1(C)C(S(O)(=O)=O)=CC=CC=1>C1C=CC=CC=1>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:10]1[S:11][CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH2:16][CH2:15][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)=[O:8]

Komponenten

5

Edukt 3

HCID 69252-Methylbenzenesulfonic acidHCID 75212-VinylpyridineHCID 20443Di(2-thienyl)acetic acid

Produkt 1

HCID 86589915Dithiophenylacetic Acid, 2-(2-pyridinyl)ethyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

The crude product of newly synthesized dithiophenyl acetic acid (10 g, 59 mmol theoretically), freshly distilled 2-vinylpyridine (6.25 g, 59 mmol), and 1 mol % toluene sulfonic acid were dissolved in benzene and placed in a round bottom flask equipped with a vigreaux column and magnetic stirbar. The reaction was then heated to reflux and allowed to react for 16 hours. The viscous liquid that remained after the solvent was removed was then purified by column chromatography (silica 2/1 v/v hexane/ethyl acetate). Yield=3.9 g. 1H NMR (CDCl3) δ=3.042 (t, 2 H), δ=3.573 (t, 2 H), δ=4.233 (s, 2H ) δ=6.968-7.476 (m, 8H), δ=8.467, (d, 1H). 13C NMR (CDCl3) δ=35.627 (CH2), δ=36.180 (CH2), δ=58.323 (CH2), δ=121.932 (CH), δ=123.383 (CH2), δ=127.501 (CH), δ=128.818 (CH), δ=129.346 (CH), δ=137.272 (C), δ=149.668 (CH), δ=159.305 (C), δ=235.369 (C═S).

Aufarbeitung

  1. customplaced in a round bottom flask
  2. customequipped with a vigreaux column and magnetic stirbar
  3. temperatureThe reaction was then heated
  4. temperatureto reflux
  5. customto react for 16 hours
  6. customwas removed
  7. customwas then purified by column chromatography (silica 2/1 v/v hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-c38a814f41cc4b92a236e4eefc635c9c
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855840B2

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