Ethanol → HCID 20271271, compound

HRID 1389787Notes

Reaction equation

HRID 1389787 reaction equation
C[O-].[Na+].C(O)C.Cl.[N:8]1[CH:13]=[CH:12][C:11]([CH2:14]Cl)=[CH:10][CH:9]=1.[SH:16][CH2:17][CH:18]([OH:21])[CH2:19][OH:20]>CO>[OH:21][CH:18]([CH2:19][OH:20])[CH2:17][S:16][CH2:14][C:11]1[CH:12]=[CH:13][N:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 702Ethanol2×HCID 7291ThioglycerolHCID 745704-(Chloromethyl)pyridinium chlorideHCID 10942334Sodium Methoxide

Product 1

HCID 20271271HCID 20271271, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (3.24 g., 60 mmoles) was dissolved in 36 ml. of absolute ethanol under a nitrogen atmosphere and the stirred solution cooled in an ice bath. With continued cooling, finely divided 4-picolyl chloride hydrochloride (5.07 g., 30 mmoles), slurried in approximately 35 ml. of absolute ethanol, was added over 15 minutes, followed by a solution to 3-mercapto-1,2-propanediol (3.24 g., 30 mmoles) in 6 ml. of absolute alcohol added dropwise over approximately 5 minutes. The reaction mixture was left to warm to room temperature and stirred overnight (16 hours). The reaction mixture was clarified by filtration through diatomaceous earth; the insolubles and the diatomaceous earth were extracted with ethanol, the original filtrate combined with the extract, and the whole concentrated to an oil (5.83 g.). Vacuum distillation, which appeared to produce considerable degradation, gave approximately 2.0 ml. of reasonably pure product (b.p. 230° C./0.3 mm.). The distillate was taken up in cold methanol, a solid impurity removed by filtration, and purified 4-(2,3-dihydroxy-1-propylthiomethyl)pyridine recovered by evaporating the filtrate to an oil (2.15 g.; ir (film): 2.97, 3.46, 3.50, 6.21, 7.05, 9.40 and 12.25μ).

Workup

  1. temperatureWith continued cooling
  2. waitThe reaction mixture was left
  3. filtrationThe reaction mixture was clarified by filtration through diatomaceous earth
  4. extractionthe insolubles and the diatomaceous earth were extracted with ethanol
  5. concentrationthe whole concentrated to an oil (5.83 g.)
  6. distillationVacuum distillation, which
  7. customto produce considerable degradation
  8. customgave approximately 2.0 ml
  9. customa solid impurity removed by filtration
  10. custompurified 4-(2,3-dihydroxy-1-propylthiomethyl)pyridine
  11. customrecovered
  12. customby evaporating the filtrate to an oil (2.15 g.; ir (film): 2.97, 3.46, 3.50, 6.21, 7.05, 9.40 and 12.25μ)

Sources & evidence

ORD record
ord-6a02c2a85f384ce3aa45ebed1c8d0767
Source dataset
uspto-grants-1981_01
Patent number
US04246263

Reaction notes

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