Water → 3-(methoxymethyl)pyridine

HRID 1005375Notes

Reaction equation

HRID 1005375 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1.[H-].[Na+].I[CH3:12].O>O1CCCC1>[CH3:12][O:1][CH2:2][C:3]1[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 75103-PyridinemethanolHCID 24758Sodium hydride

Product 1

HCID 3389263-(methoxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-hydroxymethylpyridine (10 g, 92 mmol) in anhydrous tetrahydrofuran (200 ml), under an atmosphere of nitrogen, was treated with sodium hydride (4 g of a 55% oil dispersion, 92 mmol) in portions. After stirring for 15 minutes iodomethane (5.7 ml, 92 mmol) was added dropwise and the reaction mixture was stirred at ambient temperature for 2 hours. Water (20 ml) was added and the tetrahydrofuran evaporated. The residue was partitioned between water (50 ml) and dichloromethane (70 ml). The organic layer was separated, dried (sodium sulphate) then evaporated. The crude product was purified by column chromatography on silica using ethyl acetate. The title compound was obtained (11 g, 93%) as an oil, δH (250 MHz, CDCl3) 3.42 (3H, s), 4.48 (2H, s), 7.27-7.32 (1H, m), 7.66-7.71 (1H, m), 8.53-8.60 (2H, m).

Workup

  1. additionwas added dropwise
  2. customthe tetrahydrofuran evaporated
  3. customThe residue was partitioned between water (50 ml) and dichloromethane (70 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (sodium sulphate)
  6. customthen evaporated
  7. customThe crude product was purified by column chromatography on silica

Sources & evidence

ORD record
ord-851e06dd801c4fc3807b95b8707281b1
Source dataset
uspto-grants-2000_04
Patent number
US06054469

Reaction notes

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