Pyridine → 1-(2-p-Toluenesulphonyloxyethyl)cyclopropanol

HRID 1591049Notes

Reaction equation

HRID 1591049 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([OH:7])[CH2:6][CH2:5]1.N1C=CC=CC=1.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>ClCCl>[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([O:1][CH2:2][CH2:3][C:4]2([OH:7])[CH2:6][CH2:5]2)(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 133068711-(2-Hydroxyethyl)cyclopropan-1-ol

Product 1

HCID 197661081-(2-p-Toluenesulphonyloxyethyl)cyclopropanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 1-(2-hydroxyethyl)cyclopropanol (1.31 g) and pyridine (4 ml) in dichloromethane (20 ml) was added p-toluenesulphonyl chloride (4.7 g). The mixture was then stirred at room temperature under an atmosphere of nitrogen for 5 hours before being partitioned between ether (100 ml) and water. The organic layer was washed consecutively with 1N hydrochloric acid, water, 5% sodium hydrogen carbonate solution, and brine, and dried. Concentration in vacuo gave a residue which was purified by chromatography (150 g silica gel; 40% ethyl acetate in petroleum ether as eluant) to give the 1-(2-p-toluenesulphonyloxyethyl)cyclopropanol [E; n=1, R1 +R2 =--(CH2)2 --] as an oil.

Workup

  1. custombefore being partitioned between ether (100 ml) and water
  2. washThe organic layer was washed consecutively with 1N hydrochloric acid, water, 5% sodium hydrogen carbonate solution, and brine
  3. customdried
  4. concentrationConcentration in vacuo
  5. customgave a residue which
  6. customwas purified by chromatography (150 g silica gel; 40% ethyl acetate in petroleum ether as eluant)

Sources & evidence

ORD record
ord-d1172cd6f8a743b0b9f969f47e2d2211
Source dataset
uspto-grants-1993_04
Patent number
US05206229

Reaction notes

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