Hydrochloric Acid → (3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-acetaldehyde

HRID 1802746

반응식

HRID 1802746 반응식
C[O:2][CH:3]=[CH:4][C:5]1[C:6]([CH3:17])=[N:7][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:9]=1[CH3:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.Cl>C(O)(C)C.O>[CH3:17][C:6]1[C:5]([CH2:4][CH:3]=[O:2])=[C:9]([CH3:10])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:7]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 671580974-(2-methoxy-vinyl)-3,5-dimethyl-1-phenyl-1H-pyrazole

생성물 1

HCID 57899262(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-acetaldehyde수율 60.5%

시약·촉매·용매 1

HCID 21889133Propan-2-ol--water (1/1)용매

반응 조건

온도
60 °C

실험 절차

To a stirred solution of 4-(2-methoxy-vinyl)-3,5-dimethyl-1-phenyl-1H-pyrazole (7.09 g, 31.1 mmol) in 100 mL isopropanol-water (1:1 v/v) was added p-toluenesulfonic acid monohydrate (1.5 g, 7.76 mmol). After the reaction was heated at 60° C. for 1611, 1.9 mL concentrated hydrochloric acid was added and the reaction mixture was heated at 60° C. for 20 h. The organic solvent was removed in vacuo and the remaining aqueous suspension was neutralized with an aqueous sodium bicarbonate solution and extracted several times with a dichloromethane-ethyl acetate mixture. The combined organic extracts were dried over magnesium sulfate and concentrated in vacuo to produce a residue, which was purified via silica gel column chromatography (0-50% ethyl acetate in heptane) to give the title compound as a yellow solid (4.02 g, 18.8 mmol, 60% yield).

후처리

  1. additionwas added
  2. customThe organic solvent was removed in vacuo
  3. extractionextracted several times with a dichloromethane-ethyl acetate mixture
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto produce a residue, which
  7. customwas purified via silica gel column chromatography (0-50% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-07a51c940da54e1db94c5bd20e8c9d61
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08349883B2

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