Pyridine → 3-(Methylthio)propyl 4-methylbenzenesulfonate

HRID 1267526Notes

Reaction equation

HRID 1267526 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][OH:6].N1C=CC=CC=1.C(Cl)(Cl)Cl.[S:17](Cl)([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]>C(Cl)Cl>[S:17]([O:6][CH2:5][CH2:4][CH2:3][S:2][CH3:1])([C:20]1[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=1)(=[O:19])=[O:18]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 73974-Toluenesulfonyl chlorideHCID 104483-(Methylthio)-1-propanol

Product 1

HCID 153109983-(Methylthio)propyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-methylthio-1-propanol (17) (5.0 g, 47.1 mmol), pyridine (7.43 g, 94.0 mmol) and CHCl3 (47 mL) cooled in an ice bath, tosyl chloride (13.47 g, 70.6 mmol) was added in portions with stirring. The mixture was allowed to warm to room temperature after 1 hour and stirring was continued for an additional 15 hours. The mixture was diluted with CH2Cl2 (200 mL), washed with water (2×100 mL), and the organic phase as dried (Na2SO4). The solvent was evaporated and the resulting yellow oil purified by column chromatography (silica gel, 15 wt % ether/hexanes, 50 wt % ether/hexanes), to give a colorless oil (10.5 g, 86 wt %), namely 3-methylthio-1-propanol tosylate.

Workup

  1. temperaturecooled in an ice bath
  2. stirringstirring
  3. washwashed with water (2×100 mL)
  4. dry with materialthe organic phase as dried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe resulting yellow oil purified by column chromatography (silica gel, 15 wt % ether/hexanes, 50 wt % ether/hexanes)

Sources & evidence

ORD record
ord-498fd601d67d42c68ce69cb1421edd57
Source dataset
uspto-grants-2003_04
Patent number
US06552103B1

Reaction notes

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