Ethyl p-chlorobenzalpyruvate → Ethyl 4-(4-chlorophenyl)-2-oxobutanoate

HRID 1032044Notes

Reaction equation

HRID 1032044 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([CH:6]=[CH:7][C:8](=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1>[PdH2]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8](=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:15][CH:16]=1

Participants

3

Reactant 1

HCID 54351366Ethyl p-chlorobenzalpyruvate

Product 1

HCID 13201328Ethyl 4-(4-chlorophenyl)-2-oxobutanoate

Reagents, catalysts & solvents 1

HCID 13628823Pd(II)-hydrideCatalyst

Procedure

To the ethyl p-chlorobenzalpyruvate from step B (23.6 g, 0.1 moL) was added 0.1 g of the palladium catalyst from Example 1. The reactor was pressurized to 10 psi with H2 for two hours after which time the catalyst was removed by filtration and the ethyl 4-(p-chlorophenyl)-2-ketobutanoate isolated by vacuum concentration in quantitative yield. 3H NMR (CDCl3) δ: 1.1 (t, 3H), 3.8 (m, 4H), 4.0 (q, 2H), 7.1 (s, 4H), IR (film) cm-1 : 3450w, 3075-2875s, 1750s, 1710s, 1600m, 675s.

Workup

  1. customafter which time the catalyst was removed by filtration

Sources & evidence

ORD record
ord-a49ee0c0f2df4541a94e9a9a523cad7a
Source dataset
uspto-grants-1990_09
Patent number
US04956490

Reaction notes

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