Methyl iodide → 3-(1-Ethyl-1-methoxy-propyl)-2-methyl-pyridine

HRID 1592423Notes

Reaction equation

HRID 1592423 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:13])([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[OH-].[Na+].[CH3:16]I>CN(C=O)C>[CH2:9]([C:8]([C:7]1[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=1)([O:13][CH3:16])[CH2:11][CH3:12])[CH3:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 672728223-(2-Methyl-pyridin-3-yl)-pentan-3-ol

Product 1

HCID 672722723-(1-Ethyl-1-methoxy-propyl)-2-methyl-pyridineYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(2-methyl-pyridin-3-yl)-pentan-3-ol (0.444 g, 2.48 mmol) and NaOH (0.125 g, 5.2 mmol) in DMF (13 mL) was stirred for 16 h. MeI (0.55 g, 3.9 mmol) was added. The mixture was stirred for 6 h, and the solvent was removed by evaporation under vacuum. Brine (25 mL) was added, and the aqueous mixture was extracted with CH2Cl2 (4×25 mL). The combined organic layers were dried over anhydrous Na2SO4. After filtration the solvent was removed by evaporation under vacuum, and the residue was purified by flash chromatography on a silica gel column (1:1 Et2O/CH2Cl2), affording 3-(1-ethyl-1-methoxy-propyl)-2-methyl-pyridine (0.176 g, 37%). 1H NMR (CDCl3) δ 0.73 (t, 6H, J=7.5 Hz), 1.87-2.04 (m, 4H), 2.77 (s, 3H), 3.01 (s, 3H), 7.09 (dd, 1H, J=8.1, 4.8 Hz), 7.56 (dd, 1H, J=8.1, 1.5 Hz), 8.40 (dd, 1H, J=4.8, 1.5 Hz).

Workup

  1. customthe solvent was removed by evaporation under vacuum
  2. additionBrine (25 mL) was added
  3. extractionthe aqueous mixture was extracted with CH2Cl2 (4×25 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationAfter filtration the solvent
  6. customwas removed by evaporation under vacuum
  7. customthe residue was purified by flash chromatography on a silica gel column (1:1 Et2O/CH2Cl2)

Sources & evidence

ORD record
ord-10047cbcebdb410e84661dfee773410c
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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