2-Bromopropane → HCID 14154268, compound

HRID 621800Notes

Reaction equation

HRID 621800 reaction equation
[OH:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+].Br[CH:18]([CH3:20])[CH3:19]>CN(C=O)C>[CH3:19][CH:18]([O:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8])[CH3:20]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 54711834Methyl 3-hydroxy-1H-pyrrole-2-carboxylate

Product 1

HCID 14154268HCID 14154268, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 3-hydroxy-1H-pyrrole-2-carboxylate (2.0 g, 0.014 moles) is dissolved in DMF (15 mL) under nitrogen. Potassium carbonate (2.8 g, 0.020 moles) is added followed by 2-bromopropane (5 mL, 0.05 moles) and the mixture is stirred at room temperature for 18 hours, then at 50° C. for 3 hours, then stirred into ice water (400 mL). The mixture is extracted with CH2Cl2 (3x) and the combined extracts are washed with brine (2x) and dried over MgSO4. Removal of the solvent under reduced pressure leaves the crude product as a crystalline residue. Recrystallization from ether gave the pure product (1.6 g); mp 77°-79° C.

Workup

  1. waitat 50° C. for 3 hours
  2. extractionThe mixture is extracted with CH2Cl2 (3x)
  3. washthe combined extracts are washed with brine (2x)
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent under reduced pressure
  6. customleaves the crude product as a crystalline residue
  7. customRecrystallization from ether

Sources & evidence

ORD record
ord-173dd1dd47f8439a90ac607fa674e498
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

Loading…