3-Pyridinecarboxaldehyde → HCID 54142624, compound

HRID 1981164Notes

Reaction equation

HRID 1981164 reaction equation
[Cl:1][C:2]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])=[O:7].[N:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=1.C[O-].[Na+]>CO>[Cl:1][C:2]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:3]=1[O:4][C:5]([C:6](=[O:7])[C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:23][C:19]1[CH:18]=[N:17][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 10942334Sodium MethoxideHCID 13475810HCID 13475810, compound

Product 1

HCID 54142624HCID 54142624, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In this example 5.0 grams (0.019 mole) of t-butyl 2,4-dichlorophenoxymethyl ketone and 2.1 ml (0.022 mole) of 3-pyridinecarboxaldehyde are added to 50 ml of methanol containing 0.1 g of sodium methoxide. The mixture is then stirred at room temperature for 5 hours and then evaporated to remove the methanol solvent, affording a semi-solid residue. The residue was then partitioned between diethyl ether and water. The separated ethyl ether phase was then extracted sequentially with 1N. aqueous sodium hydroxide, washed three times with water and then one time with brine. The diethyl ether phase was then dried over magnesium sulfate, filtered, then concentrated in vacuo affording a yellow oil. The yellow oil was then chromatographed on silica gel eluting with hexane ethyl acetate mixtures. The chromatographed fractions were combined by a thin layer chromatographed profile and then concentrated by evaporation affording the title compound as a viscous oil, 5.9 g.

Workup

  1. customevaporated
  2. customto remove the methanol solvent
  3. customaffording a semi-solid residue
  4. customThe residue was then partitioned between diethyl ether and water
  5. extractionThe separated ethyl ether phase was then extracted sequentially with 1N
  6. washaqueous sodium hydroxide, washed three times with water
  7. dry with materialThe diethyl ether phase was then dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customaffording a yellow oil
  11. customThe yellow oil was then chromatographed on silica gel eluting with hexane ethyl acetate mixtures
  12. customchromatographed profile
  13. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5d3512af990c48da87336da67133a852
Source dataset
uspto-grants-1985_04
Patent number
US04512995

Reaction notes

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