Benzyl acetone → 4,6-Dimethyl-5-benzyl-1H-pyridin-2-one

HRID 353350

反応式

HRID 353350 の反応式
C(N(CC)CC)C.[C:8]([NH2:14])(=[O:13])[CH2:9][C:10]([CH3:12])=O.[CH2:15]([CH2:22][C:23](=O)[CH3:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])(O)=O.[Na+]>>[CH3:12][C:10]1[C:22]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:23]([CH3:24])[NH:14][C:8](=[O:13])[CH:9]=1

参加物

4

反応物 3

HCID 17355Benzyl acetoneHCID 516892Sodium BicarbonateHCID 22022043Acetoacetamide triethylamine

生成物 1

HCID 220220554,6-Dimethyl-5-benzyl-1H-pyridin-2-one収率 53.8%

反応条件

温度
125 °C

実験手順

To a mixture of PPA (10 g) and acetoacetamide triethylamine (2.02 g, 20 mmol) was added benzylacetone (5.92 g, 5.98 mL, 40 mmol). The resulting mixture was heated at 125° C. for 3 hours. The brown mixture was poured onto crushed ice and neutralized with solid NaHCO3. The mixture was filtered to give a yellow solid, which was purified by flash column (silica, 10% MeOH/DCM) to give the pyridinone (2.29 g, 53.8%) as a yellow solid. 1H NMR (CDCl3) δ 2.07 (s, 3H), 2.37 (s, 3H), 3.81 (s, 2H), 6.38 (s, 1H), 7.00-7.40 (m, 5H); MS (CI) m/z 214.1 (MH+).

後処理

  1. additionThe brown mixture was poured
  2. customonto crushed ice
  3. filtrationThe mixture was filtered
  4. customto give a yellow solid, which
  5. customwas purified by flash column (silica, 10% MeOH/DCM)

出典と根拠

ORDレコード
ord-6c33104299ac4b9c929d28b4743a15f3
出典データセット
uspto-grants-2004_06
特許番号
US06750350B2

関連ノート

読み込み中…