Nitrogen → Benzyl 4-ethoxycarbonylmethoxybutyrate

HRID 487489Notes

Reaction equation

HRID 487489 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[N+](=[CH:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N-].N#N>[Cu].C1CCCCC1>[CH2:21]([O:20][C:18]([CH2:17][O:1][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:6])=[O:19])[CH3:22]

Participants

6

Reactant 3

HCID 947NitrogenHCID 12192Ethyl diazoacetateHCID 14443958Benzyl 4-hydroxybutanoate

Product 1

HCID 18991532Benzyl 4-ethoxycarbonylmethoxybutyrate

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8078CyclohexaneSolvent2×

Procedure

65 g (0.33 mol) of benzyl 4-hydroxybutyrate and 260 mg of copper powder are charged to 120 ml of cyclohexane and the mixture is heated to reflux. Then a mixture of 38.7 ml (0.37 mol) of ethyl diazoacetate and 300 ml of cyclohexane are added, whereupon evolution of N2 ensues. The reaction mixture is stirred for 4 hours under reflux and then for 4 hours at room temperature, filtered over a glass fibre filter and concentrated by evaporation. The residue is chromatographed on silica gel with hexane/ethyl acetate 4:1, giving benzyl 4-ethoxycarbonylmethoxybutyrate as a colourless liquid.

Workup

  1. temperaturethe mixture is heated to reflux
  2. temperatureunder reflux
  3. waitfor 4 hours at room temperature
  4. filtrationfiltered over a glass fibre
  5. filtrationfilter
  6. concentrationconcentrated by evaporation
  7. customThe residue is chromatographed on silica gel with hexane/ethyl acetate 4:1

Sources & evidence

ORD record
ord-c64a5e4c4e5c468fbf78a15e26caa6f7
Source dataset
uspto-grants-1994_03
Patent number
US05294734

Reaction notes

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