4-Toluenesulfonyl chloride → 2-[3-(Trifluoromethyl)-1H-pyrazol-1-yl]ethyl 4-methylbenzenesulfonate

HRID 1477599Notes

Reaction equation

HRID 1477599 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:7]=[CH:6][N:5]([CH2:8][C:9]([O:11]CC)=O)[N:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+].C(N(CC)CC)C.[C:36]1([CH3:46])[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1>ClCCl.O1CCCC1>[CH3:46][C:36]1[CH:41]=[CH:40][C:39]([S:42]([O:11][CH2:9][CH2:8][N:5]2[CH:6]=[CH:7][C:3]([C:2]([F:1])([F:14])[F:15])=[N:4]2)(=[O:44])=[O:43])=[CH:38][CH:37]=1

Participants

8

Reactant 5

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 24436Sodium SulfateHCID 2064143HCID 2064143, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 1178401392-[3-(Trifluoromethyl)-1H-pyrazol-1-yl]ethyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a tetrahydrofuran solution (4 mL) of the crude product of ethyl 2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]acetate synthesized in Reference Synthesis Example 53, lithium aluminum hydride (40 mg, 1.05 mmol) was added at 0° C. and the resultant solution was stirred for 3 hours. After completion of the reaction, saturated sodium sulfate aqueous solution was added to the reaction solution and the resultant mixture was dried over anhydrous magnesium sulfate and filtered. The obtained filtrate was concentrated under reduced pressure. Subsequently, to a dichloromethane solution (2 mL) of the obtained residue, triethylamine (80 μL, 0.57 mmol) and p-toluenesulfonyl chloride (300 mg, 1.57 mmol) were added and the resultant mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure and used in the next reaction.

Workup

  1. additionwas added at 0° C.
  2. additionwas added to the reaction solution
  3. dry with materialthe resultant mixture was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe obtained filtrate was concentrated under reduced pressure
  6. concentrationThe reaction solution was concentrated under reduced pressure
  7. customused in the next reaction

Sources & evidence

ORD record
ord-1948fb16d7594e849b2852af986e0358
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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