4,4-Dimethoxy-2-butanone → HCID 14253092, compound

HRID 580316Notes

Reaction equation

HRID 580316 reaction equation
Cl.[CH2:2]([C:6]1[N:11]=[C:10]([C:12]([NH2:14])=[NH:13])[CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5].[O-]CC.[Na+].[Na].CO[CH:22](OC)[CH2:23][C:24](=O)[CH3:25]>C(O)C.CC(C)=O.CCCCCC.C(O)(=O)C>[CH2:2]([C:6]1[N:11]=[C:10]([C:12]2[N:14]=[C:24]([CH3:25])[CH:23]=[CH:22][N:13]=2)[CH:9]=[CH:8][CH:7]=1)[CH2:3][CH2:4][CH3:5]

Participants

9

Reactant 4

HCID 2285484,4-Dimethoxy-2-butanoneHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 14253091HCID 14253091, compound

Product 1

HCID 14253092HCID 14253092, compoundYield 68%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 180AcetoneSolventHCID 702EthanolSolvent2×HCID 8058HexaneSolvent

Procedure

To 6-n-butyl-2-picoline amidine hydrochloride (3 g) were added sodium ethoxide solution in ethanol prepared from ethanol (100 ml) and metallic sodium (0.65 g) and then 1,1-dimethoxy-3-butanone (purity 90 %, 2.16 g). The mixture was heated under refluxing for three hours, and was left to stand at room temperature. After acetic acid was added into the mixture to be weak acidic condition, the mixture was concentrated under reduced pressure. The residue was dissolved in chloroform (200 ml), followed by washing with water (50 ml) and drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue obtained was subjected to silica gel column chromatography (eluent; hexane:acetone=2:1) to obtain 2-(6-n-butyl-2-pyridinyl)-4-methylpyrimidine (2.17 g, yield: 68 %).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder refluxing for three hours
  3. waitwas left
  4. customto stand at room temperature
  5. concentrationthe mixture was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in chloroform (200 ml)
  7. washby washing with water (50 ml)
  8. dry with materialdrying over anhydrous magnesium sulfate and concentration under reduced pressure
  9. customThe residue obtained

Sources & evidence

ORD record
ord-f967e3caf01a43ad8850bf1de6e90e14
Source dataset
uspto-grants-1988_06
Patent number
US04752608

Reaction notes

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