p-Toluenesulfonic acid → ethyl 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxylate

HRID 526764노트

반응식

HRID 526764 반응식
[I:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.[CH3:12][C:13]1C=C[C:16](S(O)(=O)=O)=[CH:17][CH:18]=1.C1C[O:26]CC1>>[I:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH:16]2[CH2:17][CH2:18][CH2:13][CH2:12][O:26]2)[N:3]=1

참가 물질

4

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 178469927HCID 178469927, 화합물

생성물 1

HCID 58486565ethyl 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxylate수율 98%

실험 절차

A solution of ethyl 3-iodo-1H-pyrazole-4-carboxylate (27 g, 101.8 mmol), 3,4-DHP (25.71 g 305.6 mmol) and PTSA (1.94 g 10.18 mmol) in THF (100 mL) was heated at 60° C. for 5 h. Solvent was evaporated under vacuum and the residue redissolved in DCM (500 mL) was added. The solution was washed with sat.NaHCO3 (200 mL×2), dried, concentrated to afford crude ethyl 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carboxylate (35 g, yield: 98%). The crude material was used in the next synthetic step without further purification.

후처리

  1. customSolvent was evaporated under vacuum
  2. dissolutionthe residue redissolved in DCM (500 mL)
  3. additionwas added
  4. washThe solution was washed
  5. dry with materialNaHCO3 (200 mL×2), dried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0a3d5917023e49e2b847a3bbf801dc33
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346761B2

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