Reaction #91543

ord-a37bdc801ed24874919533c44e84e722

Reaction equation

CCc1ccncc1
4-ethylpyridine
O=S(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+]
ammonium peroxydisulfate
O=S(=O)(O)O
sulphuric acid
O=C([O-])O.[Na+]
sodium bicarbonate
→
CCc1ccnc(CO)c1
title compound
CCc1ccnc(CO)c1
(4-ethyl-2-pyridinyl)methanol

Reactants

CCc1ccncc1
4-ethylpyridine
O=S(=O)([O-])OOS(=O)(=O)[O-].[NH4+].[NH4+]
ammonium peroxydisulfate
O=S(=O)(O)O
sulphuric acid
O=C([O-])O.[Na+]
sodium bicarbonate

Reagents

None

Solvents

CO
methanol
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Extractionextracted with chloroform (4×500 ml)
  2. 2
    DryingThis was dried over sodium sulphate
  3. 3
    Concentrationconcentrated in vacuo
  4. 4
    Otherpurified through silica using 0-60% ethyl acetate in hexane

Procedure

A solution of 4-ethylpyridine (Commercial, e.g. Sigma-Aldrich) (10.7 g), ammonium peroxydisulfate (45.6 g) and concentrated sulphuric acid (4.5 ml) in methanol (150 ml)/water (70 ml) was refluxed for 24 h. The reaction mixture was slowly added onto aqueous sodium bicarbonate and extracted with chloroform (4×500 ml). This was dried over sodium sulphate, concentrated in vacuo and purified through silica using 0-60% ethyl acetate in hexane to give the title compound, 1.16 g Mass Spec: [MH]+=138.0

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09447074B2uspto-grants-2016_09