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

HRID 224883Notes

Reaction equation

HRID 224883 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1.[CH:16](OCC)=[O:17].[H-].[Na+]>COCCOC>[CH:16]([CH:10]([CH2:9][C:6]1[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:17]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 12799555Ethyl 3-(6-methoxy-3-pyridyl)propionate

Product 1

HCID 12788663Ethyl 2-formyl-3-(6-methoxy-3-pyridyl)propionateYield 70%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of ethyl 3-(6-methoxy-3-pyridyl)propionate (32.74 g) and ethyl formate (17.22 g) was added dropwise over 1.5 hours to a stirred suspension of sodium hydride in oil (50%. 9.38 g) in 1,2-dimethoxyethane (50 ml) cooled to -2°, allowed to stand overnight at room temperature and was poured on to ice. The mixture was extracted with ether (discarded), and the aqueous phase was adjusted to pH 5 with 2 N sulphuric acid. An oil was precipitated and crystallised on standing to give ethyl 2-formyl-3-(6-methoxy-3-pyridyl)propionate (25.9 g, 70%) m.p. 91.5°-94°. A sample recrystallised from aqueous ethanol had m.p. 93°-94°.

Workup

  1. temperaturecooled to -2°
  2. additionwas poured on to ice
  3. extractionThe mixture was extracted with ether (discarded)
  4. customAn oil was precipitated
  5. customcrystallised

Sources & evidence

ORD record
ord-4db6c71e31194570af8a79e478e91636
Source dataset
uspto-grants-1980_11
Patent number
US04234588

Reaction notes

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