2-Methyl-5-hydroxypyridine → (S)-2-Methyl-5-oxiranylmethoxy-pyridine

HRID 40630

Reaction equation

HRID 40630 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[N+](C1C=C(S(O[CH2:24][C@H:25]2[O:27][CH2:26]2)(=O)=O)C=CC=1)([O-])=O>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:24][C@@H:25]2[CH2:26][O:27]2)=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 142752-Methyl-5-hydroxypyridineHCID 24758Sodium hydrideHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester

Product 1

HCID 59686824(S)-2-Methyl-5-oxiranylmethoxy-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Methyl-pyridin-3-ol (0.218 g, 2.0 mmol) was placed in a flask with DMF (10 mL) and NaH (60% dispersion in oil, 77 mg, 2.0 mmol) and stirred for 30 min. at room temperature. (S)-glycidyl 3-nitrobenzene sulfonate (0.52 g, 2.0 mmol) was then added to the reaction mixture, which was then stirred at room temperature for 14 hours. The reaction was quenched with NaHCO3 (saturated) and then extracted three times with ethyl acetate. The organic layer was dried with magnesium sulfate, filtered and the solvent was evaporated under reduced pressure to yield crude product which was purified by silica gel chromatography (60% Ethyl acetate/heptane) to yield the title compound as a residue.

Workup

  1. stirringwas then stirred at room temperature for 14 hours
  2. customThe reaction was quenched with NaHCO3 (saturated)
  3. extractionextracted three times with ethyl acetate
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customto yield crude product which
  8. customwas purified by silica gel chromatography (60% Ethyl acetate/heptane)

Sources & evidence

ORD record
ord-9bf078de8aa64806aabfd30258c40a4a
Source dataset
uspto-grants-2013_09
Patent number
US08530475B2

Linked notes

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