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

HRID 1607796Notes

Reaction equation

HRID 1607796 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

Into a sufficiently nitrogen-substituted vessel, 0.40 g (3.0 mmol) of (-)-2-fluoroheptanol and 1.00 g (13 mmol) of dry pyridine were charged andstirred under cooling with ice for 30 min. The solution was charged with 0.69 g (3.6 mmol) of p-toluenesulfonic acid chloride and further stirred for 5 hours. After the reaction, 10 ml of 1N-HCl was added, followed by two times of extraction with 10 ml of methylene chloride. Then, the extract liquid was once washed with 10 ml of distilled water. The resultant methylene chloride solution was dried with anhydrous sodium sulfate added in an appropriate amount, and the solvent was distilled off to obtain 0.59 g (2.0 mmol) of (+)-2-fluoroheptyl p-toluenesulfonate at a yield of 66%.

Workup

  1. temperatureunder cooling with ice for 30 min
  2. additionwas added
  3. extractionfollowed by two times of extraction with 10 ml of methylene chloride
  4. washThen, the extract liquid was once washed with 10 ml of distilled water
  5. dry with materialThe resultant methylene chloride solution was dried with anhydrous sodium sulfate
  6. additionadded in an appropriate amount
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-12008c51fc724ac3a89f36a6d30be378
Source dataset
uspto-grants-1989_09
Patent number
US04867903

Reaction notes

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