4-Chlorobenzenesulfonyl chloride → HCID 18424427, compound
Reaction equation
[F:1][CH2:2][C:3]([CH2:7][F:8])([OH:6])[C:4]#[CH:5].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.[H-].[Na+].CCCCCC.CC>O1CCCC1>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O:6][C:3]([CH2:7][F:8])([C:4]#[CH:5])[CH2:2][F:1])(=[O:18])=[O:17])=[CH:12][CH:11]=1Participants
Procedure
An amount (1.2 g) of 1-fluoro-2-fluoromethyl-3-butyn-2-ol and p-chlorobenzenesulfonyl chloride (2.1 g) were dissolved in tetrahydrofuran (10 ml); to the solution under cooling with ice, 60% oily sodium hydride (0.48 g) was added under a nitrogen atmosphere. After the end of the addition, the mixture was stirred for 4 hours while its temperature was raised to room temperature. A hexane/ethane mixed solvent (1/1) was added to the reaction mixture, which was then washed with water and a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane/methylene chloride=1/1) and then recrystallized from methylene chloride/hexane to give the titled compound (2.2 g).
Workup
- additionwas added under a nitrogen atmosphere
- additionAfter the end of the addition
- washwas then washed with water
- dry with materiala saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customrecrystallized from methylene chloride/hexane
Sources & evidence
- ORD record
- ord-e85547b9b0774313a6024f9ccff191b6
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06455708B1
Reaction notes
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