Methanol → 3-(2-Ethoxy-2-oxoethyl)pyridine-1-oxide ethyl iodide

HRID 1844012Notes

Reaction equation

HRID 1844012 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[N+:8]([O-:12])[CH:9]=[CH:10][CH:11]=1)[CH3:2].[I:14][CH2:15][CH3:16].CO>C(Cl)(Cl)Cl>[CH2:15]([I:14])[CH3:16].[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:7]=[N+:8]([O-:12])[CH:9]=[CH:10][CH:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 6340IodoethaneHCID 42103603-Pyridineacetic acid, ethyl ester, 1-oxide

Product 1

HCID 899646883-(2-Ethoxy-2-oxoethyl)pyridine-1-oxide ethyl iodideYield 59%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-(2-Ethoxy-2-oxoethyl)pyridine-1-oxide (I-67a: 4.8 g, 26.66 mmol) in iodoethane (7.67 mL, 95.99 mmol) was stirred at room temperature for 144 hours under nitrogen atmosphere. The reaction was monitored by TLC (10% methanol in chloroform). The reaction mass was concentrated under reduced pressure to afford 5.3 g of the crude product.

Workup

  1. concentrationThe reaction mass was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ae326f8fcba5473db0f15e2b46186ccc
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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