Tetrahydrofuran → HCID 53682870, compound

HRID 1090848Notes

Reaction equation

HRID 1090848 reaction equation
[C:1]([C:9]1[NH:10][CH:11]=[CH:12][C:13]=1[CH2:14][CH2:15][CH:16]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[H-].[Na+].[Br:34]N1C(=O)CCC1=O>O>[C:1]([C:9]1[NH:10][CH:11]=[CH:12][C:13]=1[CH2:14][CH2:15][C:16]([Br:34])([C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 67184N-bromobutanimideHCID 53958697HCID 53958697, compound

Product 1

HCID 53682870HCID 53682870, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cold solution of a compound of formula IV, preferably 2-benzoyl-[3,3-di(ethoxycarbonyl)propyl]pyrrole, in an aprotic polar solvent, such as tetrahydrofuran, is added a slight excess of a strong base, preferably sodium hydride. The reaction mixture is allowed to stir for about 30 minutes. To the reaction mixture is then added a halogenating agent, preferably N-bromosuccinimide. The reaction mixture is allowed to stir until complete The mixture is poured into water and extracted with an aprotic polar solvent, such as diethyl ether. The organic layers are combined, washed with water and brine, dried, and concentrated under reduced pressure. The residue may be purified by conventional means to produce a compound of formula VII, preferably 2-benzoyl-[3-bromo-3,3-di(ethoxycarbonyl)propyl]pyrrole.

Workup

  1. stirringto stir until complete The mixture
  2. extractionextracted with an aprotic polar solvent, such as diethyl ether
  3. washwashed with water and brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue may be purified by conventional means

Sources & evidence

ORD record
ord-34d9c7ca0e7941d09581c1980266221e
Source dataset
uspto-grants-1992_01
Patent number
US05082951

Reaction notes

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