Pentanal → HCID 5370211, compound

HRID 330606Notes

Reaction equation

HRID 330606 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][CH2:15][CH3:16]>>[CH:12](/[N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[CH:13]\[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 8063PentanalHCID 11430Potassium CarbonateHCID 31268Pyrrolidine

Product 1

HCID 5370211HCID 5370211, compoundYield 85.7%

Procedure

To 200 mL (170.4 g, 2.40 mol) of rapidly stirred pyrrolidine at 3° C., under argon, was added 100 g (0.72 mmol) of potassium carbonate followed by 127 mL (102.9 g, 1.19 mol) of valeraldehyde dropwise over 75 min. After stirring at 3°-5° C. for 6 hr, the suspension was stored at ca. 0° C. for 64 hr, filtered and the collected solids were washed with 2×50 mL of anhydrous ether. The combined filtrates were concentrated in vacuo and the residue was distilled to give 142.32 g (85.7%) of N-[1-(E)-penten-1-yl]pyrrolidine, bp 54°-56° C. (0.6-0.7 mm Hg).

Workup

  1. waitthe suspension was stored at ca. 0° C. for 64 hr
  2. filtrationfiltered
  3. washthe collected solids were washed with 2×50 mL of anhydrous ether
  4. concentrationThe combined filtrates were concentrated in vacuo
  5. distillationthe residue was distilled

Sources & evidence

ORD record
ord-48e392d4138842f88c0306e278f17bb2
Source dataset
uspto-grants-1990_01
Patent number
US04897477

Reaction notes

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