HCID 53697717, compound → HCID 53651540, compound

HRID 1415392Notes

Reaction equation

HRID 1415392 reaction equation
[C:1]([O:7][CH2:8][O:9][C:10](=[O:26])[CH:11]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:12]([O:14]CC1C=CC=CC=1)=[O:13])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[H][H]>CN(C)C=O.[Pd]>[C:1]([O:7][CH2:8][O:9][C:10](=[O:26])[CH:11]([CH2:22][CH:23]([CH3:24])[CH3:25])[C:12]([OH:14])=[O:13])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 53697717HCID 53697717, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53651540HCID 53651540, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

34.6 grams of isobutylmalonic acid benzyl ester pivaloyloxymethyl ester were dissolved in 150 ml of dimethylformamide and hydrogenated with 3.0 g of 5% palladium/charcoal. After 1 hour, the hydrogen uptake (2160 ml) had finished. The hydrogenation mixture was filtered off from the catalyst and the filtrate evaporated in a high vacuum at room temperature. The oily residue was dissolved in a 10% aqueous sodium bicarbonate solution and extracted twice with diethyl ether. The diethyl ether extracts were rejected. The sodium bicarbonate phase was acidified at 0° with citric acid and extracted twice with diethyl ether. The combined diethyl ether extracts were washed once with water, dried over magnesium sulfate and evaporated under reduced pressure. There was obtained 21.5 g of pure isobutylmalonic acid mono-pivaloyloxymethyl ester in the form of a colorless oil.

Workup

  1. filtrationThe hydrogenation mixture was filtered off from the catalyst
  2. customthe filtrate evaporated in a high vacuum at room temperature
  3. dissolutionThe oily residue was dissolved in a 10% aqueous sodium bicarbonate solution
  4. extractionextracted twice with diethyl ether
  5. customwas acidified at 0° with citric acid
  6. extractionextracted twice with diethyl ether
  7. washThe combined diethyl ether extracts were washed once with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-59c23bc464054fe1897f0a9b022a3c10
Source dataset
uspto-grants-1977_01
Patent number
US04005073

Reaction notes

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