Benzylhydrazine dihydrochloride → 1-benzyl-5-(3,4-dihydro-2H-1-benzopyran-6-yl)-3-(trifluoromethyl)-1H-pyrazole

HRID 591076ノート

反応式

HRID 591076 の反応式
Cl.Cl.[CH2:3]([NH:10][NH2:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[O:12]1[C:17]2[CH:18]=[CH:19][C:20]([C:22](=O)[CH2:23][C:24](=O)[C:25]([F:28])([F:27])[F:26])=[CH:21][C:16]=2[CH2:15][CH2:14][CH2:13]1>C(#N)C>[CH2:3]([N:10]1[C:22]([C:20]2[CH:19]=[CH:18][C:17]3[O:12][CH2:13][CH2:14][CH2:15][C:16]=3[CH:21]=2)=[CH:23][C:24]([C:25]([F:28])([F:26])[F:27])=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

参加物

4

反応物 2

HCID 146540Benzylhydrazine dihydrochlorideHCID 708188081-(3,4-dihydro-2H-1-benzopyran-6-yl)-4,4,4-trifluorobutane-1,3-dione

生成物 1

HCID 708554551-benzyl-5-(3,4-dihydro-2H-1-benzopyran-6-yl)-3-(trifluoromethyl)-1H-pyrazole収率 39.7%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of benzylhydrazine dihydrochloride (394 mg, 2.03 mmol) and 1-(3,4-dihydro-2H-1-benzopyran-6-yl)-4,4,4-trifluorobutane-1,3-dione (49b) (500 mg, 1.84 mmol) in acetonitrile (80 mL) was refluxed for 16 hours. The mixture was concentrated in vacuo and the residue was taken up in ethyl acetate (5 mL). The organic layer was successively washed with water (10 mL) and brine (10 mL) before being dried over sodium sulfate and concentrated in vacuo. The oil was purified by preparative TLC (cyclohexane/ethyl acetate 100/0 to 90/10) to provide the desired pyrazole (49c) (260 mg, 0.73 mmol, 39%).

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. washThe organic layer was successively washed with water (10 mL) and brine (10 mL)
  3. dry with materialbefore being dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe oil was purified by preparative TLC (cyclohexane/ethyl acetate 100/0 to 90/10)

出典と根拠

ORDレコード
ord-29eb6989148f4e43b5766646a4e9aa1c
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

反応ノート

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