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

HRID 1948261ノート

反応式

HRID 1948261 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-763241b4e7c24c54b16b68ed44c6e197
出典データセット
uspto-grants-2013_03
特許番号
US08399493B2

反応ノート

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