Diketene → 1-(1,3-Dioxobutyl)pyrrolidine

HRID 1055242Notes

Reaction equation

HRID 1055242 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]=[C:7]1[O:11][C:9](=[O:10])[CH2:8]1>O1CCCC1>[N:1]1([C:9](=[O:10])[CH2:8][C:7](=[O:11])[CH3:6])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 31268Pyrrolidine

Product 1

HCID 1007221-(1,3-Dioxobutyl)pyrrolidineYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 21 ml (0.25 mol) of pyrrolidine in 50 ml tetrahydrofuran was added dropwise to a solution of 20 g of diketene (0.24 mol) in 200 ml tetrahydrofuran at −5 to 0° C. After 1 h stirring at 0° C. no more starting material was detected by thin layer chromatography. The reaction mixture was evaporated and the residue was purified by column chromatography. This gave 29.9 g (0.19 mol, 81% yield) of an oil.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ec1e43e93ef64b4d883e00360b6ccd1c
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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