Diethyl Ether → HCID 86758312, compound

HRID 2227881Notes

Reaction equation

HRID 2227881 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]([O:25][CH2:26][CH3:27])=[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]([O:25][CH2:26][CH3:27])=[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 3283Diethyl EtherHCID 8082PiperidineHCID 22667308MonoethylmethylmalonateHCID 86758311HCID 86758311, compound

Product 1

HCID 86758312HCID 86758312, compoundYield 85.4%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Under a nitrogen atmosphere, 0.306 g of tert-butyl (±)-trans-2,2-dimethyl-3-formyl-cyclopropanecarboxylate was dissolved in 3 mL of anhydrous pyridine. Two hundred sixty-three milligrams (0.263 mg) of piperidine and 0.352 g of ethyl methylmalonate was then added thereto, and the resulting mixture was stirred at a temperature of 100° C. for a time period of 5 hours. 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 solvent was a mixture of n-hexane and ethyl acetate at a volume to volume ratio of 3:1 to give 0.372 g of tert-butyl (±)-trans-2,2-dimethyl-3-{2-ethoxycarbonyl-(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-ddc0a1b25dd44f74b18efb43b4610ffa
Source dataset
uspto-grants-2002_07
Patent number
US06414181B1

Reaction notes

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