4-Toluenesulfonyl chloride → HCID 21848616, compound

HRID 618889Notes

Reaction equation

HRID 618889 reaction equation
[F:1][C:2]([F:17])([C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[CH:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)O.[H-].[Na+].[S:20](Cl)([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]>C1COCC1>[F:1][C:2]([F:17])([C:10]([F:16])([F:15])[C:11]([F:14])([F:13])[F:12])[CH:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)[S:20]([C:23]1[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 104006151H-Pyrrol-2-yl(perfluoropropyl)methanol

Product 1

HCID 21848616HCID 21848616, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 2-(2',2',3',3',4',4',4'-heptafluoro-1'-hydroxybutyl)pyrrole (2.6514 g, 10 mmol) dissolved in 25 ml of dry THF is transferred by canula to a suspension of sodium hydride (0.2640 g, 11 mmol) in 50 ml of THF. The mixture is stirred for 2 hours at room temperature. A solution of tosylchloride (11 mmol) in 10 ml of THF is added dropwise and the solution stirred overnight. The resulting suspension is evaporated almost to dryness and 50 ml of water is added. The mixture was extracted 3×50 mL with pentane and the organic layers were combined and dried over magnesium sulfate. The mixture is filtered and the solvent evaporated to yield the product 2-(2',2',3',3',4',4',4'-heptafluoro-1'-tosylbutyl)pyrrole.

Workup

  1. stirringthe solution stirred overnight
  2. customThe resulting suspension is evaporated almost to dryness and 50 ml of water
  3. additionis added
  4. extractionThe mixture was extracted 3×50 mL with pentane
  5. dry with materialdried over magnesium sulfate
  6. filtrationThe mixture is filtered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-e51e6b0a2dcf424d83388bd09faa34d2
Source dataset
uspto-grants-1999_09
Patent number
US05955603

Reaction notes

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