Hydrochloric Acid → (+)-2-Fluoroheptyl p-toluenesulfonate

HRID 486346Notes

Reaction equation

HRID 486346 reaction equation
[F:1][CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH2:3][OH:4].N1C=CC=CC=1.[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.Cl>>[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22]([O:4][CH2:3][CH:2]([F:1])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:24])=[O:23])=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 15918973(-)-2-Fluoroheptanol

Product 1

HCID 14716844(+)-2-Fluoroheptyl p-toluenesulfonateYield 66.7%

Procedure

In a vessel sufficiently replaced with nitrogen, 0.40 g (3.0 mmol) of (-)-2-fluoroheptanol and 1.00 g (13 mmol) of dry pyridine were placed and dried for 30 min. under cooling on an ice bath. Into the solution, 0.69 g (3.6 mmol) of p-toluenesulfonyl chloride was added, and the mixture was stirred for 5 hours. After the reaction, 10 ml of 1N-HCl was added, and the resultant mixture was subjected to two times of extraction with 10 ml of methylene chloride. The extract liquid was washed once with 10 ml of distilled water and dried with an appropriate amount of anhydrous sodium sulfate, followed by distilling-off of the solvent to obtain 0.59 g (2.0 mmol) of (+)-2-fluoroheptyl p-toluenesulfonate.

Workup

  1. customdried for 30 min.
  2. temperatureunder cooling on an ice bath
  3. additionwas added
  4. extractionthe resultant mixture was subjected to two times of extraction with 10 ml of methylene chloride
  5. washThe extract liquid was washed once with 10 ml of distilled water
  6. dry with materialdried with an appropriate amount of anhydrous sodium sulfate

Sources & evidence

ORD record
ord-07799b6bfc5f4d089276f22db1840be2
Source dataset
uspto-grants-1994_03
Patent number
US05292453

Reaction notes

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