Butanal → 1-(But-1-enyl)pyrrolidin-2-one

HRID 389161

Reaction equation

HRID 389161 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[CH:7](=O)[CH2:8][CH2:9][CH3:10].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C=CC=CC=1>[CH:7]([N:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6])=[CH:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 261ButanalHCID 120252-PyrrolidoneHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 5801701-(But-1-enyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-pyrrolidone (50 g, 0.588 mol), butanal (42.4 g, 0.588 mol) and P2O5 (2 g, 0.014 mol) in 300 ml toluene, were refluxed together for 10 hours using Dean-Stark apparatus to collect liberated water. The resulting solution was cooled and washed with 5% solution of sodium bicarbonate and dried over anhydrous sodium sulphate. After removing the solvent under reduced pressure, 1-(but-1-enyl)pyrrolidin-2-one (I) was obtained by distillation as a liquid. (68.2 g, 83.2%). 1H NMR (CDCl3): δ 1.02 (3H, t), 2.03-2.15 (4H, m), 2.45 (2H, t), 3.5 (2H, t), 5.01 (1H, m), and 6.85 (1H, d). 13C-NMR (CDCl3): δ 172.52, 122.91, 113.8, 45.09, 31.07, 23.03, 17.27, and 14.27. IR: 2962, 2930, 1698, 1663, 1253 Cm−1.

Workup

  1. customto collect
  2. temperatureThe resulting solution was cooled
  3. washwashed with 5% solution of sodium bicarbonate
  4. dry with materialdried over anhydrous sodium sulphate
  5. customAfter removing the solvent under reduced pressure

Sources & evidence

ORD record
ord-63712aad596b488cae5aa61a515a1751
Source dataset
uspto-grants-2013_02
Patent number
US08378110B1

Linked notes

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