Hydrochloric Acid → HCID 86745006, compound

HRID 2249011Notes

Reaction equation

HRID 2249011 reaction equation
[F:1][C:2]1[C:7]([C@@H:8]([OH:10])[CH3:9])=[C:6]([F:11])[C:5]([F:12])=[C:4]([F:13])[C:3]=1[F:14].[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(N(CC)CC)C.Cl>CCOCC>[CH3:15][S:16]([O:10][C@H:8]([C:7]1[C:2]([F:1])=[C:3]([F:14])[C:4]([F:13])=[C:5]([F:12])[C:6]=1[F:11])[CH3:9])(=[O:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 6993305S(-)-1-(PENTAFLUOROPHENYL)ETHANOL

Product 1

HCID 86745006HCID 86745006, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an ice-cooled solution of 0.21 g (1 mmol) of (S)-(-)-1-(pentafluorophenyl)ethanol and 0.17 g (1.5 mmol) of methanesulfonyl chloride in 2 m(of ether, was added dropwise 0.22 m((1.6 mmol) of triethylamine. After it was stirring for two hours at room temperature, 1N hydrochloric acid was added to the reaction mixture and was extracted with ether. This ether solution was washed with 1N hydrochloric acid and an aqueous solution of 5 wt% potassium carbonate , and the solvent was distilled off under reduced pressure. The subsequent distillation gave 0.24 g (yield: 83%) of (S)-(-)-1-(pentafluorophenyl)ethyl methanesulfonate having the aforementioned physical properties.

Workup

  1. extractionwas extracted with ether
  2. washThis ether solution was washed with 1N hydrochloric acid
  3. distillationan aqueous solution of 5 wt% potassium carbonate , and the solvent was distilled off under reduced pressure
  4. distillationThe subsequent distillation

Sources & evidence

ORD record
ord-af6fd32cc21e4a2bb4f90e213a92cc3c
Source dataset
uspto-grants-1991_08
Patent number
US05041641

Reaction notes

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