Pyridine → HCID 15858643, compound

HRID 1838896Notes

Reaction equation

HRID 1838896 reaction equation
[F:1][C:2]([F:15])([C:11]([F:14])([F:13])[F:12])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][OH:10].N1C=CC=CC=1.[C:22]1([CH3:32])[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>O>[S:28]([C:25]1[CH:26]=[CH:27][C:22]([CH3:32])=[CH:23][CH:24]=1)([O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([F:15])([F:1])[C:11]([F:12])([F:13])[F:14])(=[O:30])=[O:29]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 113682968,8,9,9,9-Pentafluorononan-1-ol

Product 1

HCID 15858643HCID 15858643, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.0 g of 8,8,9,9,9-pentafluorononan-1-ol are dissolved in 26 ml of abs. pyridine, 3.1 g of p-toluenesulphonyl chloride are added at 0° C. and the mixture is stirred in the cold for 1.5 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 4.1 g of 8,8,9,9,9-pentafluorononyl tosylate as a clear oil.

Workup

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

Sources & evidence

ORD record
ord-1b89c1439cb049c98fd5cdc8b513aae0
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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