Methyl iodide → Ethyl 2-(pyridin-4-yl)propanoate

HRID 852751Notes

Reaction equation

HRID 852751 reaction equation
[Li]N([Si](C)(C)C)[Si](C)(C)C.[N:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:12]=1.[CH3:23]I>C1COCC1>[N:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 736321Ethyl pyridine-4-acetateHCID 178418261HCID 178418261, compound

Product 1

HCID 11651240Ethyl 2-(pyridin-4-yl)propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of LiN(TMS)2 (Aldrich, 1.0 M solution in THF, 30 mL, 30 mmol) in THF (30 mL) was added ethyl 4-pyridylacetate (Aldrich, 4.7 mL, 30 mmol)) at 0° C. Methyl iodide (Aldrich, 2.4 mL, 38 mmol) was added 30 min later. After 1 h, the reaction mixture was concentrated in vacuo. The crude product was purified by silica gel chromatography. Mass Spec. m/z+ion 180 (M+1).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-223a33a2cad344f3b3bcba4e652529e1
Source dataset
uspto-grants-2007_08
Patent number
US07253196B2

Reaction notes

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