Sodium methanethiolate → 4-(3-Methylsulfanyl-propyl)-pyridine

HRID 1894387Notes

Reaction equation

HRID 1894387 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9]OS(C)(=O)=O)=[CH:3][CH:2]=1.[CH3:15][S-:16].[Na+]>CO>[CH3:15][S:16][CH2:9][CH2:8][CH2:7][C:4]1[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 866300214-Pyridinepropanol, 4-methanesulfonate

Product 1

HCID 207278704-(3-Methylsulfanyl-propyl)-pyridineYield 44.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methanesulfonic acid 3-pyridin-4-yl-propyl ester (6.5 g, 30.19 mmol) in methanol (150 mL) was added sodium thiomethoxide (6.35 g, 90.57 mmol, Aldrich). The mixture was stirred at room temperature for 1 h then concentrated in vacuo. The residue was diluted with ethyl acetate and washed with water (2×), brine (1×), dried over anhydrous sodium sulfate and concentrated to give 4-(3-methylsulfanyl-propyl)-pyridine as dark brown oil (2.24 g).

Workup

  1. concentrationthen concentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water (2×), brine (1×)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d938b545e9804ec2aa78102faca9c002
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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