4-Toluenesulfonyl chloride → HCID 21848616, compound

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

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.