Methyl iodide → 4-(2-Methoxyethylthiomethyl)pyridine

HRID 485063Notes

Reaction equation

HRID 485063 reaction equation
[H-].[Na+].[OH:3][CH2:4][CH2:5][S:6][CH2:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.[CH3:14]I>O1CCCC1>[CH3:14][O:3][CH2:4][CH2:5][S:6][CH2:7][C:8]1[CH:9]=[CH:10][N:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54050Ristianol

Product 1

HCID 202713094-(2-Methoxyethylthiomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (170 mg., 7.1 mmoles, from 340 mg. of 50% dispersion in oil washed, under nitrogen, with hexane) was slurried in 5 ml. of dry tetrahydrofuran. A solution of 4-(2-hydroxyethylthiomethyl)pyridine (1.0 g., 5.9 mmoles) in 10 ml. was added dropwise over 5 minutes and the mixture stirred for 5 minutes. Finally, methyl iodide (260 mg., 0.1 ml., 5.9 mmoles) in 2 ml. of tetrahydrofuran was added and the mixture stirred overnight. The reaction mixture was clarified by filtration and evaporated to an oil (approximately 1.3 g.) which was chromatographed on silica gel with chloroform as eluent. Pure fractions of product were combined and concentrated to yield 4-(2-methoxyethylthiomethyl)pyridine [210 mg. of oil; m/e 183; pnmr/CDCl3 /TMS/delta: 7.4 (t, 2H), 6.7 (s, 3H), 6.5 (t, 2H), 6.3 (s, 2H), 2.7 (d, 2H), 1.4 (d, 2H)].

Workup

  1. additionwas added dropwise over 5 minutes
  2. stirringthe mixture stirred overnight
  3. filtrationThe reaction mixture was clarified by filtration
  4. customevaporated to an oil (approximately 1.3 g.) which
  5. customwas chromatographed on silica gel with chloroform as eluent
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-385fc10a1d634b428bfe22ccbd10895b
Source dataset
uspto-grants-1985_08
Patent number
US04535084

Reaction notes

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