Pyridine → HCID 19766114, compound

HRID 1591051Notes

Reaction equation

HRID 1591051 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.N1C=CC=CC=1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>ClCCl>[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23]([O:1][CH2:2][CH2:3][C:4]2([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 275048cyclohexaneethanol, 1-hydroxy-

Product 1

HCID 19766114HCID 19766114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice-cooled solution of 1-(2-hydroxyethyl)cyclohexanol (11.2 g) and pyridine (17 ml) in dichloromethane (100 ml) was added p-toluenesulphonyl chloride (19.5 g). The mixture was then stirred at room temperature under an atomosphere of nitrogen for 3 hours before being partitioned between ether (300 ml) and water. The organic layer was washed consecutively with 4N hydrochloric acid, water, 5% sodium hydrogen carbonate solution, and brine, and dried. Concentration in vacuo gave a residue which was purified by chromatography (500 g silica gel; 20% ethyl acetate in petroleum ether as eluant) to give 1-(2-p-toluenesulphonyloxyethyl)cyclohexanol [E; n=1, R1 +R2 =--(CH2)5 --] as an oil.

Workup

  1. custombefore being partitioned between ether (300 ml) and water
  2. washThe organic layer was washed consecutively with 4N 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 (500 g silica gel; 20% ethyl acetate in petroleum ether as eluant)

Sources & evidence

ORD record
ord-445dee1215114532b3a3ee018e8f36ac
Source dataset
uspto-grants-1993_04
Patent number
US05206229

Reaction notes

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