Water → 1-Fluoro-2-fluoromethyl-3-butyn-2-yl p-toluenesulfonate

HRID 1282422Notes

Reaction equation

HRID 1282422 reaction equation
[F:1][CH2:2][C:3]([CH2:7][F:8])([OH:6])[C:4]#[CH:5].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.[H-].[Na+].O>O1CCCC1>[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([O:6][C:3]([CH2:7][F:8])([C:4]#[CH:5])[CH2:2][F:1])(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 184244281-Fluoro-2-fluoromethyl-3-butyn-2-ol

Product 1

HCID 865875531-Fluoro-2-fluoromethyl-3-butyn-2-yl p-toluenesulfonateYield 81.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

An amount (6.6 g) of 1-fluoro-2-fluoromethyl-3-butyn-2-ol and p-toluenesulfonyl chloride (9.5 g) were dissolved in tetrahydrofuran (100 ml); to the solution under cooling with ice, 60% oily sodium hydride (2.4 g) was added under a nitrogen atmosphere. After the end of the addition, the mixture was stirred for 5 hours while its temperature was raised to room temperature. To the reaction mixture, water was added 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; hexane/methylene chloride=1/1) to give the titled compound (11.1 g).

Workup

  1. additionwas added under a nitrogen atmosphere
  2. additionAfter the end of the addition
  3. extractionfollowed by extraction with ether
  4. washThe extract was washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-380437d51a6243a090b10b8b1f58005b
Source dataset
uspto-grants-2002_09
Patent number
US06455708B1

Reaction notes

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