Acetic Anhydride → 4-(2-Acetoxyethylthiomethyl)pyridine

HRID 485062Notes

Reaction equation

HRID 485062 reaction equation
[OH:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[C:12]([O:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[CH:7]=[CH:8][N:9]=[CH:10][CH:11]=1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 54050Ristianol

Product 1

HCID 202712834-(2-Acetoxyethylthiomethyl)pyridine

Procedure

4-(2-Hydroxyethylthiomethyl)pyridine (1.0 g.) was refluxed with 10 ml. of acetic anhydride for 3 hours. After standing overnight at room temperature, the acetic anhydride was evaporated in vacuo, the residue diluted with 10 ml. of water, made basic with sodium bicarbonate, and the product extracted into chloroform (four times 50 ml.). The chloroform was carbon treated, dried and concentrated to an oil (1.47 g.). The oil was chromatographed on 60 g. of silica gel with 5% methanol/chloroform as eluant. Fractions containing only product (Rf 0.6 on thin layer silica gel chromatography eluted with 18:1 chloroform:methanol) were combined and concentrated to yield 4-(2-acetoxyethylthiomethyl)pyridine [300 mg. of oil; pnmr/CDCl3 /TMS/delta: 7.9 (s, 3H), 7.3 (t, 2H), 6.3 (s, 2H), 5.8 (t, 2H), 2.7 (d, 2H), 1.4 (d, 2H)].

Workup

  1. customthe acetic anhydride was evaporated in vacuo
  2. additionthe residue diluted with 10 ml
  3. extractionthe product extracted into chloroform (four times 50 ml.)
  4. additiontreated
  5. customdried
  6. concentrationconcentrated to an oil (1.47 g.)
  7. customThe oil was chromatographed on 60 g
  8. additionFractions containing only
  9. washproduct (Rf 0.6 on thin layer silica gel chromatography eluted with 18:1 chloroform:methanol)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-61caaee5cb5a42cfa3b8d0190693cb54
Source dataset
uspto-grants-1985_08
Patent number
US04535084

Reaction notes

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