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

HRID 127195Notes

Reaction equation

HRID 127195 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°, and allowed to stand overnight at room temperature. The mixture was poured on to ice and the mixture was extracted with ether (discarded), and the aqueous phase was adjusted to pH 5 with 2N 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. additionThe mixture was poured on to ice
  3. extractionthe mixture was extracted with ether (discarded)
  4. customAn oil was precipitated
  5. customcrystallised

Sources & evidence

ORD record
ord-a67b02fa4d8d4fe8a92a3c55c260c582
Source dataset
uspto-grants-1981_03
Patent number
US04255428

Reaction notes

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