Acetone → HCID 17971929, compound

HRID 1726856Notes

Reaction equation

HRID 1726856 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10]([O:12]CC)=O)[CH:5]=1.[CH3:15][C:16]([CH3:18])=[O:17].[ClH:19]>O1CCCC1.O>[Cl:19][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([C:10](=[O:12])[CH2:15][C:16](=[O:17])[CH2:18][C:10]([C:6]2[CH:5]=[C:4]([Cl:3])[CH:9]=[CH:8][N:7]=2)=[O:12])[CH:5]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 130153594-Chloropyridine-2-carboxylic acid ethyl ester

Product 1

HCID 17971929HCID 17971929, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

4 g (0.1 mol. about 60% dispersion) of sodium hydride in 100 ml of absolute tetrahydrofuran are placed in a reaction vessel under a nitrogen atmosphere. At <56° C., a solution of 18.5 g (0.1 mol) of ethyl 4-chloropyridine-2-carboxylate and 2.32 g (0.04 mol) of dried acetone in 75 ml of THF is added dropwise over the course of two hours. The red suspension is then carefully poured into 900 ml of water. It is rendered neutral with 6N HCl, tetrahydrofuran is distilled off on a rotary evaporator, and the yellow to beige 1,5-bis(4-chloropyridin-2-yl)pentane-1,3,5-trione formed is filtered off. The dried, sparingly soluble product is processed further without any particular purification steps. IR (cm−1): 1619 (m); 1564 (s); 1546 (s); 1440 (m); 1374 (s); 1156 (m); 822 (w).

Workup

  1. distillationis distilled off on a rotary evaporator

Sources & evidence

ORD record
ord-860e499132ce4c0293e1c52b2d766d58
Source dataset
uspto-grants-2009_02
Patent number
US07494964B2

Reaction notes

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