Sodium Methoxide → HCID 86662981, compound

HRID 1398229Notes

Reaction equation

HRID 1398229 reaction equation
Cl[C:2]1[C:7]([C:8]2[O:12][C:11]([CH3:13])=[N:10][CH:9]=2)=[CH:6][CH:5]=[C:4]([Cl:14])[N:3]=1.[CH3:15][O-:16].[Na+]>CO>[Cl:14][C:4]1[N:3]=[C:2]([O:16][CH3:15])[C:7]([C:8]2[O:12][C:11]([CH3:13])=[N:10][CH:9]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866629825-(2,6-Dichloro-3-pyridyl)-2-methyloxazole

Product 1

HCID 86662981HCID 86662981, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 2,6-dichloro-3-(2-methyl-1,3-oxazol-5-yl)pyridine (2.22 g) in methanol (25 mL) was added sodium methoxide (5M methanol solution, 1.9 mL) at room temperature, and the mixture was stirred under a nitrogen atmosphere over the weekend. The reaction mixture was concentrated and diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was separated, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and separated by HPLC (column: Chiralpak AD, mobile phase: hexane/2-propanol) to give the title compound (867 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  8. customseparated by HPLC (column: Chiralpak AD, mobile phase: hexane/2-propanol)

Sources & evidence

ORD record
ord-55116d5f1388435bad243e44d0473e24
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

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