Diethylamine → (E)-N,N-Diethyl-4-oxo-2-pentenamide

HRID 1637721Notes

Reaction equation

HRID 1637721 reaction equation
[O:1]=[C:2]([CH3:8])/[CH:3]=[CH:4]/[C:5](Cl)=[O:6].[CH2:9]([NH:11][CH2:12][CH3:13])[CH3:10]>CCOCC>[CH2:9]([N:11]([CH2:12][CH3:13])[C:5](=[O:6])/[CH:4]=[CH:3]/[C:2](=[O:1])[CH3:8])[CH3:10]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 132966864-Oxopent-2-enoic chloride

Product 1

HCID 18799723(E)-N,N-Diethyl-4-oxo-2-pentenamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-15 °C

Procedure

To flame dried flask containing (E)-4-oxo-2-pentenoyl chloride (1.16 g, 8.76 mmol) in ether cooled to -15° C. is added diethylamine (1.41 g, 19.28 mmol) in ether (5 ml) and stirred for 2 hours while being warmed to ambient temperature. The solvents are removed in vacuo, and chromatographed on silica gel (230-400 mesh, 100 ml), eluting with hexane/ethyl acetate (75/25). The appropriate fractions are combined (Rf =0.31, TLC, hexane/ethyl acetate, 25/75) and concentrated in vacuo to give the title compound, NMR (CDCl3) 7.15, 7.04, 3.45, 3.40, 2.33, 1.20, 1.15.

Workup

  1. temperatureTo flame
  2. customdried flask
  3. temperaturewhile being warmed to ambient temperature
  4. customThe solvents are removed in vacuo
  5. customchromatographed on silica gel (230-400 mesh, 100 ml)
  6. washeluting with hexane/ethyl acetate (75/25)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ea3d15cfb3cc4db99e3ee18cd08829f1
Source dataset
uspto-grants-2000_03
Patent number
US06043248

Reaction notes

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