p-Toluenesulfonic acid monohydrate → (5-Methanesulfonyl-pyridin-3-yl)-propynoic acid ethyl ester

HRID 24032Notes

Reaction equation

HRID 24032 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:13][S:14]([C:17]1[CH:18]=[N:19][CH:20]=[C:21]([C:23]#[C:24][C:25](OCC)([O:29]CC)[O:26][CH2:27][CH3:28])[CH:22]=1)(=[O:16])=[O:15]>C1(C)C=CC=CC=1>[CH2:27]([O:26][C:25](=[O:29])[C:24]#[C:23][C:21]1[CH:20]=[N:19][CH:18]=[C:17]([S:14]([CH3:13])(=[O:15])=[O:16])[CH:22]=1)[CH3:28]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 225703163-Methanesulfonyl-5-triethoxyprop-1-ynyl-pyridine

Product 1

HCID 67427397(5-Methanesulfonyl-pyridin-3-yl)-propynoic acid ethyl esterYield 58.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

p-Toluenesulfonic acid monohydrate (1.39 g, 0.73 mmol) was added to a solution of 3-methanesulfonyl-5-triethoxyprop-1-ynyl-pyridine (1.20 g, 3.70 mmol) in toluene (40 mL). After stirring overnight at room temperature, the solvent was removed under reduced pressure. The crude product was chromatographed on silica (30% ethyl acetate/hexanes) to give the title compound (0.55 g, 53% yield) as a white solid. 1H NMR (CDCl3) δ 9.17 (d, 1H, J=2.4 Hz), 9.03 (d, 1H, J=2.0), 8.40 (t, 1H, J=2.0 Hz), 4.35 (q, 6H, J=8.0), 3.14 (s, 3H), 1.38 (t, 9H, J=8.0).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe crude product was chromatographed on silica (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8b9e599bea6943a1ae5e1b42d26744b1
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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