Butanal → 1-But-1-enylpyrrolidine

HRID 646604Notes

Reaction equation

HRID 646604 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH:12](=O)[CH2:13][CH2:14][CH3:15]>>[CH:12]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[CH:13][CH2:14][CH3:15]

Participants

4

Reactant 3

HCID 261ButanalHCID 11430Potassium CarbonateHCID 31268Pyrrolidine

Product 1

HCID 1396491-But-1-enylpyrrolidine

Conditions

Temperature
0 °C

Procedure

To a dry 500 milliliter (mL) three neck round bottom flask equipped with magnetic stirrer, nitrogen inlet, addition funnel, and thermometer, was charged with pyrrolidine (83.45 mL, 1.0 mmol) and potassium carbonate (34.55 g, 0.25 mol). The mixture was cooled to 0° C. and butanal (30.05 grams (g), 0.42 mol) was added dropwise with stirring under nitrogen at ad rate that maintained the temperature below 15° C. After the addition was complete (˜10 minutes), the cooling bath was taken away and the reaction mixture allowed to warm to room temperature over three hours. The reaction mixture was filtered through a scintered glass filter to remove the solids. The solid was washed thoroughly with ether, and combined with the filtrate, which was concentrated on the rotary evaporator to give the crude 1-but-1-enylpyrrolidine which was purified by vacuum distillation @15 mmHg 65-78° C.; 1H NMR (CDCl3): δ 6.20 (d, 1H), 4.18 (q, 1H), 2.95 (m, 4H), 1.80, (m, 4H), 0.97 (d, 3H).

Workup

  1. temperaturemaintained the temperature below 15° C
  2. additionAfter the addition
  3. custom(˜10 minutes)
  4. temperatureto warm to room temperature over three hours
  5. filtrationThe reaction mixture was filtered through a scintered glass
  6. filtrationfilter
  7. customto remove the solids
  8. washThe solid was washed thoroughly with ether
  9. concentrationwas concentrated on the rotary evaporator

Sources & evidence

ORD record
ord-f8a7ef105dde432fb867f800487dc20e
Source dataset
uspto-grants-2010_04
Patent number
US07705154B2

Reaction notes

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