Pyridine → HCID 14178171, compound

HRID 3930Notes

Reaction equation

HRID 3930 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH:6]([OH:14])[C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[N:11][CH:12]=1)[CH3:2].[C:16](OC(=O)C)(=[O:18])[CH3:17].N1C=CC=CC=1.[OH-].[Na+]>CN(C)C1C=CN=CC=1>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH:6]([O:14][C:16](=[O:18])[CH3:17])[C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[N:11][CH:12]=1)[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 14178170Ethyl 3-Hydroxy-3-(6-methyl-3-pyridyl)propanoate

Product 1

HCID 14178171HCID 14178171, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

4.3 g (0.021 mol) of 3-hydroxy-3-(2-methyl-5-pyridyl)-propionic acid ethyl ester, 3.0 g (0.03 mol) of acetic anhydride, 2.7 g (0.034 mol) of pyridine and 0.17 g (0.0017 mol) of 4-dimethylaminopyridine were stirred at 0° C. for 24 hours. The solution was mixed with 25 ml of 5 percent sodium hydroxide solution and extracted twice, each time with 25 ml of methylene chloride. The organic extracts were evaporated; the residue (4.7 g) contained 3-acetoxy-3-(2-methyl-5-pyridyl)-propionic acid ethyl ester (yield 90.4 percent).

Workup

  1. extractionextracted twice
  2. customThe organic extracts were evaporated

Sources & evidence

ORD record
ord-51ef9f6ae2d14a58b7d97c8023ad50fd
Source dataset
uspto-grants-1988_02
Patent number
US04723017

Reaction notes

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