Pyridine → Ethyl 4-(4-fluorophenyl)-3-oxobutanoate

HRID 2380943Notes

Reaction equation

HRID 2380943 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:17])[C:10]([C:14]([OH:16])=[O:15])=CNC=2)=[CH:4][CH:3]=1.F[C:19]1C=CC(CC(Cl)=O)=C[CH:20]=1.CC1(C)OC(=O)CC(=O)O1.N1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9](=[O:17])[CH2:10][C:14]([O:16][CH2:19][CH3:20])=[O:15])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 37449884-Fluorophenylacetyl chlorideHCID 602042075-(4-Fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid

Product 1

HCID 10585213Ethyl 4-(4-fluorophenyl)-3-oxobutanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The intermediate, 5-(4-fluorophenyl)-4-oxo-1,4-dihydropyridine-3-carboxylic acid (8) can be obtained using the chemistry described in Scheme 2. Thus, 2-(4-fluorophenyl)acetyl chloride (10) can be treated with 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum's acid) in the presence of pyridine and the resulting adduct can be refluxed in ethanol to afford ethyl 4-(4-fluorophenyl)-3-oxobutanoate (12). Treatment of intermediate 12 with triazine and sodium ethoxide in ethanol can furnish the requisite ester intermediate, which can be readily hydrolyzed in the presence of sodium hydroxide at elevated temperature to furnish intermediate 8.

Sources & evidence

ORD record
ord-caf9aa4e28c14f1792b0794121afff49
Source dataset
uspto-grants-2012_09
Patent number
US08258118B2

Reaction notes

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