Methylmalonic Acid → HCID 86758310, compound

HRID 2227880Notes

Reaction equation

HRID 2227880 reaction equation
[CH3:1][C:2]1([CH3:14])[C@H:4]([CH:5]=O)[C@@H:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].N1CCCCC1.[CH3:21][CH:22](C(O)=O)[C:23]([OH:25])=[O:24].C(OCC)C>N1C=CC=CC=1.C(OCC)(=O)C.CCCCCC>[CH3:1][C:2]1([CH3:14])[C@@H:4](/[CH:5]=[C:22](/[C:23]([OH:25])=[O:24])\[CH3:21])[C@@H:3]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

8

Reactant 4

HCID 487Methylmalonic AcidHCID 3283Diethyl EtherHCID 8082PiperidineHCID 13188342HCID 13188342, compound

Product 1

HCID 86758310HCID 86758310, compoundYield 94.1%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Under a nitrogen atmosphere, 0.165 g of tert-butyl (±)-cis-2,2-dimethyl-3-formylcyclopropanecarboxylate was dissolved in 5 mL of anhydrous pyridine. Seventeen-hundredths milliliters (0.17 mL) of piperidine and 0.197 g of methylmalonic acid was then added thereto, and the resulting mixture was stirred at a temperature of 60° C. for a time period of 1 hour. After the mixture was allowed to cool to room temperature, 100 mL of diethyl ether was added to said mixture and the resulting mixture was washed with 3N-hydrochloric acid and then saturated brine to obtain an organic layer therefrom. The organic layer was dried over anhydrous magnesium sulfate and thereafter the solvent was evaporated under reduced pressure in order to produce a residue. The residue was subjected to silica gel column chromatography, wherein the eluent was a mixture of n-hexane and ethyl acetate at a volume to volume ratio of 3:1 to give 0.199 g of tert-butyl (±)-trans-2,2-dimethyl-3-{2-carboxy-(E)-1-propenyl}cyclopropanecarboxylate.

Workup

  1. temperatureto cool to room temperature
  2. washthe resulting mixture was washed with 3N-hydrochloric acid
  3. customsaturated brine to obtain an organic layer
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure in order
  6. customto produce a residue

Sources & evidence

ORD record
ord-f82f4b9c0fbc4ceb83fe1c76f48f3812
Source dataset
uspto-grants-2002_07
Patent number
US06414181B1

Reaction notes

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