Sodium Sulfate → 2-Methoxy-3-hydroxymethyl-5-ethyl-6-methylpyridine

HRID 273680Notes

Reaction equation

HRID 273680 reaction equation
[CH3:1][O:2][C:3]1[N:12]=[C:11]([CH3:13])[C:10]([CH2:14][CH3:15])=[CH:9][C:4]=1[C:5](OC)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]([CH2:5][OH:6])=[CH:9][C:10]([CH2:14][CH3:15])=[C:11]([CH3:13])[N:12]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 15228413Methyl 2-methoxy-5-ethyl-6-methylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 152284142-Methoxy-3-hydroxymethyl-5-ethyl-6-methylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 2-methoxy-5-ethyl-6-methylnicotinate (2.28 g, 10.9 mmol) in anhydrous tetrahydrofuran (50 mL), under a nitrogen atmosphere, was added cautiously lithium aluminum hydride (0.77 g, 20 mmol). After refluxing this mixture for 15-20 hours, saturated aqueous Na2SO4 was added carefully to quench the cooled reaction mixture. This mixture was diluted with more THF, dried (Na2SO4), filtered and the solvent evaporated. This residue was chased with ethanol/toluene to remove traces of water and triturated with hexane as the product slowly crystallized out to give 1.30 g (66%), mp 53°-55° C.

Workup

  1. temperatureAfter refluxing this mixture for 15-20 hours
  2. customto quench
  3. customthe cooled reaction mixture
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customto remove traces of water
  8. customtriturated with hexane as the product
  9. customslowly crystallized out
  10. customto give 1.30 g (66%), mp 53°-55° C.

Sources & evidence

ORD record
ord-59060ee76405498a8635b8c2a9c265be
Source dataset
uspto-grants-1995_02
Patent number
US05387512

Reaction notes

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