Pyridine → 1-(2-Methoxy-2-oxoethyl)pyridinium chloride

HRID 1795458Notes

Reaction equation

HRID 1795458 reaction equation
[Cl:1]CCC([O-])=O.[N:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:13]([O:16][CH2:17]C)(=[O:15])[CH3:14]>>[Cl-:1].[CH3:17][O:16][C:13]([CH2:14][N+:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:15]

Participants

4

Reactant 3

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 69921542-Chloromethylacetate

Product 1

HCID 117692671-(2-Methoxy-2-oxoethyl)pyridinium chlorideYield 73%

Conditions

Temperature
80 °C

Procedure

In a 250 mL round-bottom flask with a stir bar was charged 2-chloromethylacetate (17.5 mL, 0.2 mol), ethyl acetate (50 mL), and pyridine (16.2 mL, 0.2 mol). The overall homogeneous solution was heated with a condenser at 80° C. for 24 h and the resulting heterogeneous white suspension was cooled to room temperature and filtrated under reduced pressure. The off-white filtrate was recrystallized from small amount of ethanol to give the title compound (27.4 g, 73%) as a white solid. MS (ES+): 152 (M)+.

Workup

  1. temperaturethe resulting heterogeneous white suspension was cooled to room temperature
  2. filtrationfiltrated under reduced pressure
  3. customThe off-white filtrate was recrystallized from small amount of ethanol

Sources & evidence

ORD record
ord-a9679273c5824c37a46557a53f507314
Source dataset
uspto-grants-2006_04
Patent number
US07026326B2

Reaction notes

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