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

HRID 349599

반응식

HRID 349599 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

The crude product of newly synthesized dithiophenyl acetic acid (10 g, 59 mmol theoretically), freshly distilled 2-vinylpyridine (6.25 g, 59 μmmol), 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, 2H), δ=3.573 (t, 2H), 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).

후처리

  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)

출처 및 근거

ORD 기록
ord-31fe1e9cace040bba4f2bde0a1dd4ad0
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179872B2

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