Tetrabutylammonium Hydroxide → 2-Trifluoromethylsulfonyloxy-4-pyridinyl 4,4,4-trifluoro-1-butanesulfonate

HRID 896835Notes

Reaction equation

HRID 896835 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6][C:7]1[CH:12]=[C:11]([OH:13])[CH:10]=[CH:9][N:8]=1)(=[O:5])=[O:4].[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.[F:34][C:35]([F:44])([F:43])[CH2:36][CH2:37][CH2:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl.O>[F:34][C:35]([F:44])([F:43])[CH2:36][CH2:37][CH2:38][S:39]([O:13][C:11]1[CH:10]=[CH:9][N:8]=[C:7]([O:6][S:3]([C:2]([F:1])([F:14])[F:15])(=[O:5])=[O:4])[CH:12]=1)(=[O:41])=[O:40]

Participants

6

Reactant 3

HCID 2723671Tetrabutylammonium HydroxideHCID 27611764,4,4-trifluorobutane-1-sulfonyl ChlorideHCID 178527628HCID 178527628, compound

Product 1

HCID 208165222-Trifluoromethylsulfonyloxy-4-pyridinyl 4,4,4-trifluoro-1-butanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Under argon, 550 mg (2.26 mmol) of 4-hydroxy-2-pyridinyl trifluoromethanesulfonate (Example 39A) are suspended in 15 ml of dichloromethane at room temperature. 2 ml of a 40% strength solution of tetrabutylammonium hydroxide in water are added dropwise to this. Then 476 mg (2.26 mmol) of 4,4,4-trifluoro-1-butanesulfonyl chloride are added and allowed to react for 20 minutes. Working up takes place by adding water, extracting with ethyl acetate, washing, drying and evaporating in a rotary evaporator. The residue is purified by chromatography on 20 g of silica gel (0.04-0.063 mm) with cyclohexane/ethyl acetate 2:1 to 1:1).

Workup

  1. customto react for 20 minutes
  2. extractionextracting with ethyl acetate
  3. washwashing
  4. customdrying
  5. customevaporating in a rotary evaporator
  6. customThe residue is purified by chromatography on 20 g of silica gel (0.04-0.063 mm) with cyclohexane/ethyl acetate 2:1 to 1:1)

Sources & evidence

ORD record
ord-8258baf336174c35a8aef1e47800008a
Source dataset
uspto-grants-2005_07
Patent number
US06919470B2

Reaction notes

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