Ethyl formate → Ethyl 2-formyl-3-(5-pyrimidyl)propionate

HRID 2228909Notes

Reaction equation

HRID 2228909 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:4]=[N:3][CH:2]=1.[CH:14](OCC)=[O:15].[H-].[Na+]>C(COC)OC.C(OCC)(=O)C>[CH:14]([CH:8]([CH2:7][C:5]1[CH:6]=[N:1][CH:2]=[N:3][CH:4]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:15]

Participants

6

Reactant 3

HCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 21936199Ethyl 3-(5-pyrimidyl)propionate

Product 1

HCID 21936283Ethyl 2-formyl-3-(5-pyrimidyl)propionate

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl 3-(5-pyrimidyl)propionate (2.28 g) and ethyl formate (1.41 ml) dissolved in dry dimethoxyethane (5 ml) was added dropwise over 30 min to a suspension of sodium hydride (60%, 4.0 g) in DME (5 ml) under nitrogen, keeping the temperature below 0° C. Stirring was continued for a further 24 h, then the mixture was poured onto ice and washed with ether. The aqueous layer was adjusted to pH 7, then evaporated and the residue extracted with acetone. Filtration and evaporation gave crude product, which was taken up in ethyl acetate, charcoaled, dried and evaporated to give ethyl 2-formyl-3-(5-pyrimidyl)propionate. Like other compounds of this type, this proved difficult to characterise and was used without further purification.

Workup

  1. customthe temperature below 0° C
  2. additionthe mixture was poured onto ice
  3. washwashed with ether
  4. customevaporated
  5. extractionthe residue extracted with acetone
  6. filtrationFiltration and evaporation
  7. customgave crude product, which
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-ba14b3a24d3346d3b1e9775151fa79f6
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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