Water → 1-Fluoro-2-fluoromethyl-3-butyn-2-yl propanesulfonate

HRID 1282431Notes

Reaction equation

HRID 1282431 reaction equation
[F:1][CH2:2][C:3]([CH2:7][F:8])([OH:6])[C:4]#[CH:5].[H-].[Na+].[CH2:11]([S:14](Cl)(=[O:16])=[O:15])[CH2:12][CH3:13].O>O1CCCC1>[CH2:11]([S:14]([O:6][C:3]([CH2:7][F:8])([C:4]#[CH:5])[CH2:2][F:1])(=[O:16])=[O:15])[CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 662791-Propanesulfonyl chlorideHCID 184244281-Fluoro-2-fluoromethyl-3-butyn-2-ol

Product 1

HCID 865875541-Fluoro-2-fluoromethyl-3-butyn-2-yl propanesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An amount (2.4 g) of 1-fluoro-2-fluoromethyl-3-butyn-2-ol was dissolved in tetrahydrofuran (20 ml); to the solution under cooling with ice, 60% oily sodium hydride (0.96 g) was added under a nitrogen atmosphere. After stirring for 30 minutes under cooling with ice, propanesulfonyl chloride (2.2 ml) was added dropwise. The mixture was stirred for 5 hours while its temperature was raised to room temperature. Water was added to the reaction mixture, followed by extraction with ether. The extract was 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; 30% ethyl acetate/hexane) to give the titled compound (4.1 g).

Workup

  1. additionwas added under a nitrogen atmosphere
  2. additionwas added dropwise
  3. stirringThe mixture was stirred for 5 hours while its temperature
  4. extractionfollowed by extraction with ether
  5. washThe extract was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-954ae96693524b9ba81221ef547c9fb0
Source dataset
uspto-grants-2002_09
Patent number
US06455708B1

Reaction notes

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