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

HRID 1948261Notes

Reaction equation

HRID 1948261 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-763241b4e7c24c54b16b68ed44c6e197
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

Loading…