Ethyl Acetate → 1-(4-chlorobenzyl)-5-(hydroxymethyl)pyridin-2(1H)-one

HRID 1948260Notes

Reaction equation

HRID 1948260 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][N:7]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]([CH:14]=[O:15])=[CH:8]2)=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.CCOC(C)=O>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:8]=[C:9]([CH2:14][OH:15])[CH:10]=[CH:11][C:12]2=[O:13])=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 866149681-(4-Chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde

Product 1

HCID 693501121-(4-chlorobenzyl)-5-(hydroxymethyl)pyridin-2(1H)-oneYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

According to Scheme 16 Method B: A solution of 1-(4-chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde (1 eq, 1.41 mmol, 0.35 g, Example 10 Step 1) and DIBAL (3 eq, 4.20 mmol, 4.20 mL) in THF (5 mL) was stirred for 30 min. at −78° C. and 1 hour at room temperature. After addition of AcOEt, the reaction mixture was diluted with water. The organic layer washed with saturated NH4Cl solution, dried over Na2SO4, filtered through celite and evaporated. The resulting crude residue was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/MeOH 95/5 to afford 1-(4-chlorobenzyl)-5-(hydroxymethyl)pyridin-2(1H)-one (0.45 mmol, 0.11 g, 32%) as an orange oil.

Workup

  1. washThe organic layer washed with saturated NH4Cl solution
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered through celite
  4. customevaporated
  5. customThe resulting crude residue was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2)

Sources & evidence

ORD record
ord-8191703085234fbe84ce50401e07a3b1
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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