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

HRID 2425544ノート

反応式

HRID 2425544 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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)+

後処理

  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

出典と根拠

ORDレコード
ord-785f54ba52934704bac387b914d79a63
出典データセット
uspto-grants-2011_06
特許番号
US07964732B2

反応ノート

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