Dichloromethane → Dimethyl-2,4-bis(phenylmethyl)-3-oxoglutarate

HRID 1078144Notes

Reaction equation

HRID 1078144 reaction equation
[C:1]1([CH:7]=[C:8]([C:13](=[O:26])[C:14](=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([O:17][CH3:18])=[O:16])[C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H].C(Cl)Cl>CO.[Pd]>[CH3:18][O:17][C:15](=[O:16])[CH:14]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:13](=[O:26])[CH:8]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 53920876HCID 53920876, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12200243Dimethyl-2,4-bis(phenylmethyl)-3-oxoglutarateYield 58.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Dimethyl 2,4-bis(phenylmethylene)-3-oxo-glutarate (630 mg, 1.8 mmol) (C. H. Chen, et al, J. Org. Chem., 1981, 46, 2752-2757) was dissolved in about 100 mL of methanol and 250 mg of 10% palladium on carbon was added. The reaction mixture was shaken at ambient temperature under 4 atmospheres of hydrogen for about 12 h. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue (750 mg) was taken up in ~15 mL of methylene chloride and applied to a 1.0×45 cm column of silica gel. The column was eluted @5 p.s.i. with 150 mL of methylene chloride to give 374 mg (58% yield) of the title compound. The 300 MHz 1H NMR was consistent with the assigned structure.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washThe column was eluted @5 p.s.i

Sources & evidence

ORD record
ord-fab9489f33c0437dad5c9213dee8eb96
Source dataset
uspto-grants-1996_08
Patent number
US05545750

Reaction notes

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