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

HRID 1655146Notes

Reaction equation

HRID 1655146 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-025c2b2e76f1414eb4f4f664bb315a29
Source dataset
uspto-grants-1993_10
Patent number
US05250219

Reaction notes

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