Diethylamine → ethyl 5-(N,N-diethylaminomethyl)-2-furoate

HRID 1701800

Reaction equation

HRID 1701800 reaction equation
Cl[CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=1.[CH2:13]([NH:15][CH2:16][CH3:17])[CH3:14]>C1C=CC=CC=1>[CH2:13]([N:15]([CH2:2][C:3]1[O:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][CH:4]=1)[CH2:16][CH3:17])[CH3:14]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 263166Ethyl 5-(chloromethyl)-2-furancarboxylate

Product 1

HCID 20346154ethyl 5-(N,N-diethylaminomethyl)-2-furoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ethyl 5-(chloromethyl)-2-furoate (0.1 mole) is refluxed with diethylamine (0.25 mole) in 40 ml of benzene for one hour. The benzene solution is filtered off and washed with water. The organic layer is separated and dried over magnesium sulfate. The magnesium sulfate is removed by filtration and the organics are evaporated to dryness. The residue is distilled to give a pure fraction of ethyl 5-(N,N-diethylaminomethyl)-2-furoate boiling at 97°-106° C. at 0.1 mm of Hg.

Workup

  1. filtrationThe benzene solution is filtered off
  2. washwashed with water
  3. customThe organic layer is separated
  4. dry with materialdried over magnesium sulfate
  5. customThe magnesium sulfate is removed by filtration
  6. customthe organics are evaporated to dryness
  7. distillationThe residue is distilled

Sources & evidence

ORD record
ord-3dc60f99f2a140ba89ca3e4738118d19
Source dataset
uspto-grants-1980_03
Patent number
US04195023

Linked notes

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