Ammonium Chloride → HCID 89586435, 화합물

HRID 1747826

반응식

HRID 1747826 반응식
[C:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=[CH:5][CH:4]=1)#[CH:2].C([Li])CCC.[C:19]1([C:25]#[C:26][CH:27]=[O:28])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>C1COCC1>[C:19]1([C:25]#[C:26][CH:27]([OH:28])[C:2]#[C:1][C:3]2[N:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:6]=[CH:5][CH:4]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 75740PhenylpropynalHCID 895863365-ethynyl-1-phenyl-1H-pyrazoleHCID 178418339Butyllithium

생성물 1

HCID 89586435HCID 89586435, 화합물수율 82.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

실험 절차

To a solution of 5-ethynyl-1-phenyl-1H-pyrazole (0.500 g) in THF (20.0 mL) was added dropwise 2.5M butyllithium in THF solution (1.55 mL) at −78° C., and the mixture was stirred for 30 min. To the reaction mixture was added dropwise a solution of 3-phenylprop-2-ynal (0.464 g) in THF (5.00 mL) at −78° C., the mixture was stirred for 45 min, and saturated aqueous ammonium chloride solution (10.0 mL) was added. The mixture was extracted with dichloromethane, the extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane/methanol) to give the title compound (0.73 g).

후처리

  1. stirringthe mixture was stirred for 45 min
  2. extractionThe mixture was extracted with dichloromethane
  3. washthe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (dichloromethane/methanol)

출처 및 근거

ORD 기록
ord-7d57d89db4b845bc934a381b30beb8c2
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150588B2

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