Acetone → 4-(4-iodo-1H-pyrazol-1-yl)cyclohexanone

HRID 511338

反応式

HRID 511338 の反応式
O1[C:5]2([CH2:10][CH2:9][CH:8]([N:11]3[CH:15]=[C:14]([I:16])[CH:13]=[N:12]3)[CH2:7][CH2:6]2)[O:4]CC1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CC(C)=O>O>[I:16][C:14]1[CH:13]=[N:12][N:11]([CH:8]2[CH2:7][CH2:6][C:5](=[O:4])[CH2:10][CH2:9]2)[CH:15]=1

参加物

5

反応物 3

HCID 180AcetoneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 595411251-(1,4-Dioxaspiro[4.5]dec-8-yl)-4-iodo-1H-pyrazole2 回

生成物 1

HCID 595411654-(4-iodo-1H-pyrazol-1-yl)cyclohexanone

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

A mixture of 1-(1,4-dioxaspiro[4.5]dec-8-yl)-4-iodo-1H-pyrazole (Compound 137F, 3.0 g, 8.9 mmol), pyridinium p-toluenesulfonate (4.5 g, 17.9 mmol), acetone (100 mL) and H2O (100 mL) was heated at 60° C. overnight. Work-up: Solvent was evaporated and the residue was extracted with EtOAc (3×60 mL). The combined extracts were washed with water (3×50 mL), brine (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound as white solid. It was used in the next step without further purification. 1H NMR (400 MHz, CDCl3): δ=2.23-2.63 (m, 8 H), 4.57-4.64 (m, 1 H), 7.51 (s, 1 H), 7.54 (s, 1 H). MS (ES+): m/z=291.09 (100). HPLC: tR=2.79 min (polar—5 min, ZQ3).

後処理

  1. customSolvent was evaporated
  2. extractionthe residue was extracted with EtOAc (3×60 mL)
  3. washThe combined extracts were washed with water (3×50 mL), brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-80f03c31f257450fb7fdd2f7858debbb
出典データセット
uspto-grants-2015_08
特許番号
US09096624B2

関連ノート

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