2,6-Lutidine → Ethyl 4-oxobutanoate

HRID 1872006Notes

Reaction equation

HRID 1872006 reaction equation
C([CH:3]([CH2:7][C:8](Cl)=[O:9])[C:4](Cl)=[O:5])C.N1C(C)=CC=C[C:12]=1[CH3:18].[O:19]1CCCC1>[Pd]>[O:9]=[CH:8][CH2:7][CH2:3][C:4]([O:5][CH2:12][CH3:18])=[O:19]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 8028TetrahydrofuranHCID 218646082-Ethylbutanedioyl dichloride

Product 1

HCID 82395Ethyl 4-oxobutanoate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Ethyl succinyl cloride (4.1 g) was added to a suspension of 10% palladium on carbon (0.3 g) and 2,6-lutidine (2.9 ml) in dry tetrahydrofuran (100 ml). The mixture was hydrogenated at 3 atmospheres pressure for 24 hours. The reaction mixture was filtered and the filtrate evaporated under reduced pressure. Yield 3.15 g. 1H NMR: δ (CDCl3) 9.82 (s,1H), 4.16 (q,2H), 2.80 (t,2H), 2.63 (t,2H), 1.26 (t,3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-848e5950e52c45569d822cdab9834ed7
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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