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

HRID 1477599
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HRID 1477599 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 24436Sodium SulfateHCID 2064143Ethyl 2-(3-(trifluoromethyl)-1H-pyrazol-1-yl)acetateHCID 21226445Aluminium lithium hydride

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1948fb16d7594e849b2852af986e0358
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09403798B2

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