1-(4-Chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde → 1-(4-chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)methyl)pyridin-2(1H)-one

HRID 1948257Notes

Reaction equation

HRID 1948257 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)C[Mg]Br.[Cl:12][C:13]1[CH:28]=[CH:27][C:16]([CH2:17][N:18]2[C:23](=[O:24])[CH:22]=[CH:21][C:20]([CH:25]=[O:26])=[CH:19]2)=[CH:15][CH:14]=1>C1COCC1>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][N:18]2[CH:19]=[C:20]([CH:25]([OH:26])[C:10]3[CH:9]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:11]=3)[CH:21]=[CH:22][C:23]2=[O:24])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 866149681-(4-Chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehydeHCID 178490219HCID 178490219, compound

Product 1

HCID 589669561-(4-chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)methyl)pyridin-2(1H)-oneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to Scheme 7 Method B: A solution of 3-methoxybenzylmagnesium bromide (1.2 eq, 1.00 mmol, 1.00 mL) was added dropwise to a solution of 1-(4-chlorobenzyl)-1,6-dihydro-6-oxopyridine-3-carbaldehyde (1 eq, 1.21 mmol, 0.30 g, Example 10 Step 1) in THF (15 mL) at −78° C. under a nitrogen atmosphere. The reaction mixture was stirred for 14 hours at room temperature. The resulting mixture was poured onto ice and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered and evaporated. Purification by flash chromatography (AIT Flashsmart prepacked column 25 g SiO2, CH2Cl2/AcOEt 80/20 to 70/30) afford 1-(4-chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)methyl)pyridin-2(1H)-one (0.64 mmol, 0.28 g, 64%) as a yellow semi-solid.

Workup

  1. additionThe resulting mixture was poured onto ice
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customPurification by flash chromatography (AIT Flashsmart prepacked column 25 g SiO2, CH2Cl2/AcOEt 80/20 to 70/30)

Sources & evidence

ORD record
ord-6bf9695163f54cbeb41029f82402e9e6
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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