Ethyl formate → Ethyl 2-formyl-3-(6-methyl-3-pyridyl)propionate

HRID 903343

Reaction equation

HRID 903343 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[CH:15](OCC)=[O:16].[H-].[Na+]>COCCOC>[CH:15]([CH:9]([CH2:8][C:5]1[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:16]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 3018102Ethyl 3-(6-methyl-3-pyridyl)propionate

Product 1

HCID 3018359Ethyl 2-formyl-3-(6-methyl-3-pyridyl)propionateYield 700.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of ethyl 3-(6-methyl-3-pyridyl)propionate (1.31 g) and ethyl formate (7.43 g) was added dropwise to a stirred suspension of sodium hydride (50% dispersion in oil, 4.07 g) in dry 1,2-dimethoxyethane (24 ml) maintained at 0°. The mixture was allowed to warm to room temperature, stirred overnight and poured into ice-water (300 g). The mixture was extracted with ether, the aqueous phase was adjusted to pH 5.4 with hydrochloric acid, and the solid which separated was collected to give ethyl 2-formyl-3-(6-methyl-3-pyridyl)propionate (10.5 g, 70%), m.p. 142°-4°.

Workup

  1. temperaturemaintained at 0°
  2. extractionThe mixture was extracted with ether
  3. customthe solid which separated
  4. customwas collected

Sources & evidence

ORD record
ord-d8f7a3681b60439d8ead92953dd9e5c7
Source dataset
uspto-grants-1980_10
Patent number
US04227000

Linked notes

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