Lithium Chloride → 1-Hexyl-4-methyl-3-nitro-5-phenyl-2-pyridone

HRID 1387282노트

반응식

HRID 1387282 반응식
[Cl-].[Li+].[CH2:3]([N:9]1[CH:14]=[C:13](I)[C:12]([CH3:16])=[C:11]([N+:17]([O-:19])=[O:18])[C:10]1=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:21]1([Sn](CCCC)(CCCC)CCCC)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1.C(OCC)(=O)C>[CH2:3]([N:9]1[CH:14]=[C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:12]([CH3:16])=[C:11]([N+:17]([O-:19])=[O:18])[C:10]1=[O:20])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

참가 물질

6

반응물 3

HCID 433294Lithium ChlorideHCID 607632TributylphenyltinHCID 217065251-Hexyl-5-iodo-4-methyl-3-nitro-2-pyridone

생성물 1

HCID 217065401-Hexyl-4-methyl-3-nitro-5-phenyl-2-pyridone수율 72.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of bis(triphenylphosphine)Pd(II) chloride (0.014 g), lithium chloride (0.067 g), 1-hexyl-5-iodo-4-methyl-3-nitro-2-pyridone (0.15 g, 0.41 mmol) and phenyltributyltin (0.11 mL, 0.62 mmol) in THF (15 mL) was heated under reflux for 2 days. The mixture was cooled, diluted with ethyl acetate, and washed with aqueous potassium fluoride and water. The organic phase was dried, filtered and evaporated. Chromatography of the residue over silica gel (petroleum ether/methylene chloride 1/1 to methylene chloride is gradient) gave 1-hexyl-4-methyl-3-nitro-5-phenyl-2-pyridone (0.093 g, 72%).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 2 days
  3. temperatureThe mixture was cooled
  4. washwashed with aqueous potassium fluoride and water
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-9b7e98136a404e32892c393e44a41e3b
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06268365B1

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