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

HRID 2194708노트

반응식

HRID 2194708 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-178ebe5f66614d05a861e3a8d840ce8d
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334301B2

반응 노트

불러오는 중…