Methyl acetoacetate → Ethyl 3,5-dioxo-4-methoxycarbonyl-2-methylhexanoate

HRID 654997Notes

Reaction equation

HRID 654997 reaction equation
[Na].[C:2]([O:8][CH3:9])(=[O:7])[CH2:3][C:4]([CH3:6])=[O:5].C(OC)(=O)CC(C)=O.C[O-].[Na+].Cl[C:22]([CH:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:23]>C1(C)C=CC=CC=1>[O:23]=[C:22]([CH:3]([C:2]([O:8][CH3:9])=[O:7])[C:4](=[O:5])[CH3:6])[CH:24]([CH3:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 10888271Ethyl 2-chloroformylpropionateHCID 10942334Sodium MethoxideHCID 87089651CID 87089651

Product 1

HCID 14348548Ethyl 3,5-dioxo-4-methoxycarbonyl-2-methylhexanoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Methyl acetoacetate sodium salt (1.24 g; 9 mmole) prepared from methyl acetoacetate and sodium methoxide was suspended in dry toluene (10 ml), and a solution of ethyl 2-chloroformylpropanoate (1.12 g; 6.8 mmole) in dry toluene (5 ml) was dropwise added thereto at room temperature. The resultant mixture was stirred at the same temperature for 1 hour, and insoluble materials were removed by filtration. The filtrate was concentrated at 40° C. under reduced pressure, and the residue was purified by silica gel column chromatography to give ethyl 3,5-dioxo-4-methoxycarbonyl-2-methylhexanoate.

Workup

  1. customat room temperature
  2. custominsoluble materials were removed by filtration
  3. concentrationThe filtrate was concentrated at 40° C. under reduced pressure
  4. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bee929924afe40e69def7f1848447ac4
Source dataset
uspto-grants-1992_07
Patent number
US05134231

Reaction notes

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