Sodium hydride → Oxolan-2-yl 1-ethenyl-2-oxopyrrolidine-3-carboxylate

HRID 1004727Notes

Reaction equation

HRID 1004727 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:12][CH2:11][N:10]([CH:13]=[CH2:14])[C:9]1=[O:15])=[O:7])([CH3:4])(C)C.[H-].[Na+].Cl[CH:19]1[CH2:23]CC[O:20]1>O1CCCC1.C(OCC)C>[O:20]1[CH2:19][CH2:23][CH2:4][CH:1]1[O:5][C:6]([CH:8]1[CH2:12][CH2:11][N:10]([CH:13]=[CH2:14])[C:9]1=[O:15])=[O:7]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 178730Furan, 2-chlorotetrahydro-HCID 15389820HCID 15389820, compound

Product 1

HCID 54014762Oxolan-2-yl 1-ethenyl-2-oxopyrrolidine-3-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

8.9 g of 3-(t-butoxycarbonyl)-1-vinyl-2-pyrrolidinone (BCVP) was dissolved in 50 ml of tetrahydrofuran free of moisture. To this solution 1.0 g of sodium hydride and 4.4 g of 2-chlorotetrahydrofuran were added and allowed to react at room temperature for 1 hour. This solution was diluted with diethylether and washed many times with pure water. The organic solvent of the organic phase was evaporated and the residue was subjected to silica gel column chromatography, to obtain 9.3 g of pure 3-(tetrahydrofuranyloxycarbonyl)-1-vinyl-2-pyrrolidinone (hereinafter referred to as "TFVP"). Its chemical structure was determined by IR spectra and NMR.

Workup

  1. customto react at room temperature for 1 hour
  2. washwashed many times with pure water
  3. customThe organic solvent of the organic phase was evaporated

Sources & evidence

ORD record
ord-edd4e1fcd2a14d3e81a0c92b3e5274e5
Source dataset
uspto-grants-2000_04
Patent number
US06051678

Reaction notes

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