Water → 5-Quinolyl trifluoromethanesulfonate

HRID 428531Notes

Reaction equation

HRID 428531 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.C([O-])([O-])=O.[K+].[K+].[O:18](S(C(F)(F)F)(=O)=O)[S:19]([C:22]([F:25])([F:24])[F:23])(=O)=[O:20].O>N1C=CC=CC=1>[F:23][C:22]([F:25])([F:24])[S:19]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2)(=[O:20])=[O:18]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67749Trifluoromethanesulfonic anhydrideHCID 135441757Quinolin-5-ol

Product 1

HCID 114714035-Quinolyl trifluoromethanesulfonateYield 91.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 5-hydroxy-quinoline (8 g, 55 mmol) and K2CO3 (15.2 g, 110 mmol) in anhydrous pyridine (60 mL) under nitrogen was cooled to −20° C. Tf2O (13.97 mL, 83 mmol) was added drop-wise via syringe. The reaction mixture was stirred 1 hour at −20° C. then warmed to 0° C. for 1 hour then stirred at ambient temperature for 48 hours. The reaction mixture was then poured into H2O (200 mL) and extracted in CH2Cl2 (2×200 mL). The aqueous layer was acidified with 1 N HCl (100 mL) and back extracted with CH2Cl2 (2×200 mL). The organic fractions were dried over Na2SO4, concentrated and purified by column chromatography (40% EtOAc/Hexanes) affording 13.97 g (90%) of the product as a pink oil: MS EI m/e 277 (M+).

Workup

  1. temperaturethen warmed to 0° C. for 1 hour
  2. stirringthen stirred at ambient temperature for 48 hours
  3. extractionextracted in CH2Cl2 (2×200 mL)
  4. extractionback extracted with CH2Cl2 (2×200 mL)
  5. dry with materialThe organic fractions were dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by column chromatography (40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-b64fa4c6023a4b978dd0551272114135
Source dataset
uspto-grants-2001_11
Patent number
US06313126B1

Reaction notes

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