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

HRID 526764ノート

反応式

HRID 526764 の反応式
[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

参加物

4

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 8028TetrahydrofuranHCID 178469927HCID 178469927、化合物

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0a3d5917023e49e2b847a3bbf801dc33
出典データセット
uspto-grants-2016_05
特許番号
US09346761B2

反応ノート

読み込み中…