Reaction #52575

Reaction equation

dithiophenyl acetic acid

2-vinylpyridine

toluene sulfonic acid

→

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

Solvents

benzene

Conditions

Workup

1. 1
   Otherplaced in a round bottom flask
2. 2
   Otherequipped with a vigreaux column and magnetic stirbar
3. 3
   TemperatureThe reaction was then heated
4. 4
   Temperatureto reflux
5. 5
   Otherto react for 16 hours
6. 6
   Otherwas removed
7. 7
   Otherwas then purified by column chromatography (silica 2/1 v/v hexane/ethyl acetate)

Procedure

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).

Source