2-Mercaptoethanol → HCID 20093199, compound

HRID 274347Notes

Reaction equation

HRID 274347 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].Cl.Cl[CH2:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1>[O-]CC.[Na+]>[N:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH2:7][S:1][CH2:2][CH2:3][OH:4])[CH:9]=1

Participants

4

Reactant 2

HCID 15672-MercaptoethanolHCID 233943-(Chloromethyl)pyridine hydrochloride

Product 1

HCID 20093199HCID 20093199, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

A stirred solution of sodium ethoxide (4.6 g of sodium in 100 ml ethanol) was treated with 2-mercaptoethanol (7.8 g, 0.1 mol) followed by 3-chloromethylpyridine hydrochloride (16.4 g, 0.1 mol). The mixture was then refluxed under argon for 3.5 hours, filtered and evaporated in vacuo and the residue purified by flash chromatography on silica, eluting with 3% methanol in ethyl acetate, to give 2-(3-pyridylmethylthio)ethanol (13 g), as a yellow oil;

Workup

  1. temperatureThe mixture was then refluxed under argon for 3.5 hours
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customthe residue purified by flash chromatography on silica
  5. washeluting with 3% methanol in ethyl acetate

Sources & evidence

ORD record
ord-fd7701e1a06c4087b37fc86241895824
Source dataset
uspto-grants-1995_02
Patent number
US05389649

Reaction notes

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