Hydrochloric Acid → 1-(5-Methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)ethanone

HRID 2425544노트

반응식

HRID 2425544 반응식
C(O[CH:4]=[C:5]([C:9](=O)[CH3:10])[C:6](=[O:8])[CH3:7])C.[F:12][C:13]([F:18])([F:17])[CH2:14][NH:15][NH2:16].Cl>CO>[CH3:10][C:9]1[N:15]([CH2:14][C:13]([F:18])([F:17])[F:12])[N:16]=[CH:4][C:5]=1[C:6](=[O:8])[CH3:7]

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 787402,2,2-TrifluoroethylhydrazineHCID 2404183-(Ethoxymethylene)pentane-2,4-dione

생성물 1

HCID 671822581-(5-Methyl-1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)ethanone수율 51%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a solution of 3-(ethoxymethylene)pentane-2,4-dione (Perkin 1. 2000, 1455-1460, 1.95 g, 12.5 mmol) in MeOH (33 ml) was added a solution of 2,2,2-trifluoroethylhydrazine (1.54 g, 13.5 mmol) and conc.HCl (2.6 ml) in MeOH (10 ml) (pre-cooled at 0° C.) dropwise at −15° C. The resulting mixture was then stirred for 24 h at rt. After removal of the solvent at rt, the residue was basified with 2N NaOH aq, and the aqueous layer was extracted several times with EtOAc. The combined organic extracts were dried over Na2SO4, and concentrated in vacuo to give the crude product as a single regioisomer (1.41 g, 51% yield). 1H NMR (300 MHz, CDCl3) δ 2.46 (3H, s), 2.62 (3H, s), 4.66 (1H, d, J=6.0 Hz), 4.72 (1H, d, J=9.0 Hz), 7.92 (1H, s). MS (ESI) m/z 207 (M+H)+

후처리

  1. customdropwise at −15° C
  2. customAfter removal of the solvent at rt
  3. extractionthe aqueous layer was extracted several times with EtOAc
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-785f54ba52934704bac387b914d79a63
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07964732B2

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