Pyridine → N-(Vinyloxycarbonyloxyethyl)pyrrolidin-2,5-dione

HRID 1460285Notes

Reaction equation

HRID 1460285 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[CH2:7][CH2:6][C:5]1=[O:10].N1C=CC=CC=1.Cl[C:18]([O:20][CH:21]=[CH2:22])=[O:19]>C(Cl)(Cl)Cl>[CH:21]([O:20][C:18]([O:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[CH2:7][CH2:6][C:5]1=[O:10])=[O:19])=[CH2:22]

Participants

5

Reactant 3

HCID 1049PyridineHCID 78808Vinyl chloroformateHCID 236334N-(2-Hydroxyethyl)succinimide

Product 1

HCID 21647323N-(Vinyloxycarbonyloxyethyl)pyrrolidin-2,5-dioneYield 40.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 500 mL 3-neck round bottom flask fitted with a mechanical stirrer, condenser, nitrogen blanket, dropping funnel, ice-saltwater bath, and thermometer were added 5.0 (35.0 mmol) of N-(2-hydroxyethyl) succinimide, 2.8 g (35.0 mmol) of pyridine, and 100 mL chloroform. To the reaction mixture was added 3.7 g (35.0 mmol) of vinyl chloroformate so that the temperature remained below 10° C. After stirring at room temperature for 18 hours the reaction mixture was washed with 100 mL 2N HCl and 100 mL 2N NaOH. The organic phase was dried over magnesium sulfate. The solvent was removed on a rotary evaporator and the resulting red liquid chromatographed (silica gel, chloroform). The recovered oil totaled 3.0 g (14.1 mmol, 40.2% yield). FTIR (neat, capillary) 1755.10, 1694.90, 1648.77, 1427.00, 1396.38, 1366.15, 1329.97, 1298.34, 1239.58, 1185.85, 1152.26, 1111.20, 1085.92, 1024.25, 1005.00, 946.53, 894.87, 882.46, 848.52, 818.51, 778.99, 700.00, 661.32. NMR (CDCl3) 6.50-6.83 (1H,q), 4.13- 4.66 (2H,m), 3.93-4.13 (2H,m), 3.33-3.66 (2H,m), 2.41 (4H,S). ##STR17##

Workup

  1. customTo a 500 mL 3-neck round bottom flask fitted with a mechanical stirrer, condenser
  2. customremained below 10° C
  3. washwas washed with 100 mL 2N HCl and 100 mL 2N NaOH
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. customThe solvent was removed on a rotary evaporator
  6. customthe resulting red liquid chromatographed (silica gel, chloroform)

Sources & evidence

ORD record
ord-1c7f90abcf5f4f09af2f3d8ef8305643
Source dataset
uspto-grants-1991_12
Patent number
US05070215

Reaction notes

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