4-Methoxyphenol → 1-(4-chlorobenzyl)-5-((4-methoxyphenoxy)methyl)pyridin-2(1H)-one

HRID 1948261노트

반응식

HRID 1948261 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](O)=[CH:5][CH:4]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.[Cl:41][C:42]1[CH:57]=[CH:56][C:45]([CH2:46][N:47]2[CH:52]=[C:51]([CH2:53][OH:54])[CH:50]=[CH:49][C:48]2=[O:55])=[CH:44][CH:43]=1>C1COCC1>[Cl:41][C:42]1[CH:43]=[CH:44][C:45]([CH2:46][N:47]2[CH:52]=[C:51]([CH2:53][O:54][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:50]=[CH:49][C:48]2=[O:55])=[CH:56][CH:57]=1

참가 물질

6

반응물 4

HCID 90154-MethoxyphenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 693501121-(4-chlorobenzyl)-5-(hydroxymethyl)pyridin-2(1H)-one

생성물 1

HCID 589668981-(4-chlorobenzyl)-5-((4-methoxyphenoxy)methyl)pyridin-2(1H)-one수율 42.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

According to Scheme 16 Method B: 4-Methoxyphenol (1.5 eq, 0.68 mmol, 84.3 mg), PPh3 (2.0 eq, 0.91 mmol, 0.30 g) and DEAD (2 eq, 0.91 mmol, 0.16 g) were added to a solution of 1-(4-chlorobenzyl)-5-(hydroxymethyl)pyridin-2(1H)-one (1 eq, 0.45 mmol, 0.11 g) in THF (5 mL). The reaction mixture was stirred overnight at room temperature. After evaporation of the solvent, the reaction mixture was diluted with water. The organic layer washed with saturated NaHCO3 solution, dried over Na2SO4, filtered and evaporated. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2) using cyclohexane/AcOEt 80/20 to afford 1-(4-chlorobenzyl)-5-((4-methoxyphenoxy)methyl)pyridin-2(1H)-one (0.19 mmol, 0.07 g, 42%) as a white solid.

후처리

  1. customAfter evaporation of the solvent
  2. additionthe reaction mixture was diluted with water
  3. washThe organic layer washed with saturated NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2)

출처 및 근거

ORD 기록
ord-763241b4e7c24c54b16b68ed44c6e197
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399493B2

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