Pyridine → 9,9,10,10,10-Pentafluorodecyltosylate

HRID 1838899Notes

Reaction equation

HRID 1838899 reaction equation
[F:1][C:2]([F:16])([C:12]([F:15])([F:14])[F:13])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][OH:11].N1C=CC=CC=1.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>O>[S:29]([C:26]1[CH:27]=[CH:28][C:23]([CH3:33])=[CH:24][CH:25]=1)([O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([F:16])([F:1])[C:12]([F:13])([F:14])[F:15])(=[O:31])=[O:30]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 234971719,9,10,10,10-Pentafluorodecan-1-ol

Product 1

HCID 572649069,9,10,10,10-Pentafluorodecyltosylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g of 9,9,10,10,10-pentafluorodecan-1-ol is dissolved in 8 ml of abs. pyridine, 985 mg of p-toluenesulphonyl chloride are added at 0° C. and the mixture is stirred in the cold for 2 hours. The reaction mixture is then added to water, extracted 3 times with ether, dried over magnesium sulphate and concentrated in vacuo. Preparative column chromatography on silica gel using a hexane-ethyl acetate gradient leads to 1.5 g of 9,9,10,10,10-penta-fluorodecyl tosylate as an oil.

Workup

  1. extractionextracted 3 times with ether
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-083f252ac53942bf865da4e3497f17c3
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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