Hydrochloric Acid → [1-phenyl-5-(phenylamino)-1H-pyrazol-3-yl]methanol

HRID 2194708ノート

反応式

HRID 2194708 の反応式
[C:1]1([N:7]2[C:11]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:10][C:9]([C:19](OCC)=[O:20])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>O1CCCC1.C1(C)C=CC=CC=1>[C:1]1([N:7]2[C:11]([NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[CH:10][C:9]([CH2:19][OH:20])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 68410675ethyl 1-phenyl-5-(phenylamino)-1H-pyrazole-3-carboxylate

生成物 1

HCID 68411083[1-phenyl-5-(phenylamino)-1H-pyrazol-3-yl]methanol収率 106.8%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution of ethyl 1-phenyl-5-(phenylamino)-1H-pyrazole-3-carboxylate (345 mg) in tetrahydrofuran (10 mL) was cooled to −78° C., and a 1.5 mol/L solution (3.7 mL) of diisobutylaluminum hydride in toluene was added dropwise. After stirring at 0° C. for 1 hr, the mixture was treated with 1 mol/L hydrochloric acid, and extracted with ethyl acetate. The extract was washed with 1 mol/L hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1→1:2) to give the title compound as a pale-yellow oil (yield 318 mg, yield quantitative).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with 1 mol/L hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=2:1→1:2)

出典と根拠

ORDレコード
ord-178ebe5f66614d05a861e3a8d840ce8d
出典データセット
uspto-grants-2012_12
特許番号
US08334301B2

反応ノート

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