Pyridine → 1-{[(Ethenyloxy)carbonyl]oxy}pyrrolidine-2,5-dione

HRID 1460284Notes

Reaction equation

HRID 1460284 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].N1C=CC=CC=1.Cl[C:16]([O:18][CH:19]=[CH2:20])=[O:17]>O1CCCC1>[CH:19]([O:18][C:16]([O:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8])=[O:17])=[CH2:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 78808Vinyl chloroformateHCID 80170N-Hydroxysuccinimide

Product 1

HCID 221167231-{[(Ethenyloxy)carbonyl]oxy}pyrrolidine-2,5-dioneYield 62.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 10.0 (87.0 mmol) of N-hydroxy succinimide, 6.9 g (87.0 mmol) of pyridine, and 100 mL tetrahydrofuran was added. To the reaction mixture 9.25 g (87.0 mmol) of vinyl chloroformate was added 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 liquid chromatographed (silica gel, chloroform) to yield 10.0 g (54.0 mmol, 62.1% yield) of an oil. FTIR (neat, capillary) 3516.50, 3132.04, 3099.40, 3003.94, 2960.21, 1830.80, 1823.25, 1792.36, 1734.05, 1671.98, 1653.62, 1646.30, 1429.97, 1380.77, 1368.60, 1306.35, 1260.89, 1241.83, 1201.12, 1162.09, 1154.49, 1134.29, 1087.59, 1049.93, 1005.21, 990.18, 948.77, 941.86, 908.06, 897.29, 892.42, 812.37, 769.04, 756.85, 724.90, 707 81. NMR (CDCl3) 6.73-7.09 (1H,q), 4.61-5.24 (2H,m), 2.78 (4H,S). ##STR16##

Workup

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

Sources & evidence

ORD record
ord-ab26af9607e644a0b0f2244be5d7a013
Source dataset
uspto-grants-1991_12
Patent number
US05070215

Reaction notes

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