Bromocyclopentane → HCID 17604933, compound

HRID 2205961Notes

Reaction equation

HRID 2205961 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[O:7].[H-].[Na+].Br[CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>CS(C)=O.C(OCC)(=O)C>[CH:11]1([N:1]2[CH:5]=[CH:4][CH:3]=[C:2]2[CH:6]=[O:7])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 8728BromocyclopentaneHCID 13854Pyrrole-2-carboxaldehydeHCID 24758Sodium hydride

Product 1

HCID 17604933HCID 17604933, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1H-pyrrole-2-carbaldehyde (12.0 g) in DMSO (252 mL) was added sodium hydride (55% dispersion in mineral oil, 8.26 g) at 0° C., and the mixture was stirred for 30 min. To the reaction mixture was added bromocyclopentane (22.6 g) at 0° C., and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate (500 mL), and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (9.34 g).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. washwashed with water and saturated brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1c93636defb64b789914b98ed8666a98
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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