Imidazole → 2-[(2-Chloro-5-ethyl pyridine-3-yl)(hydroxy)methyl]cyclopent-2-en-1-one

HRID 1445553Notes

Reaction equation

HRID 1445553 reaction equation
[Cl:1][C:2]1[N:9]=[CH:8][C:7]([CH2:10][CH3:11])=[CH:6][C:3]=1[CH:4]=[O:5].N1C=CN=C1.[C:17]1(=[O:22])[CH2:21][CH2:20][CH:19]=[CH:18]1>CO.O>[Cl:1][C:2]1[C:3]([CH:4]([OH:5])[C:18]2[C:17](=[O:22])[CH2:21][CH2:20][CH:19]=2)=[CH:6][C:7]([CH2:10][CH3:11])=[CH:8][N:9]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 135882-Cyclopenten-1-oneHCID 249768452-Chloro-5-ethylpyridine-3-carbaldehyde

Product 1

HCID 588802392-[(2-Chloro-5-ethyl pyridine-3-yl)(hydroxy)methyl]cyclopent-2-en-1-oneYield 97%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

The clear solution of 2-Chloro-5-ethylnicotinaldehyde (10 mmol, 1.69) and imidazole (10 mmol, 0.68 g) in 50 ml. of MeOH was slowly charged with 50 ml. of deionized water. To a stirred homogeneous reaction mixture was added 2-cyclopenten-1-one (10.2 mmol., 0.88 g) at room temperature and reaction progress was monitored by TLC. Upon completion of the reaction, excess MeOH was removed under reduced pressure, washed with water and extracted with CHCl3 thrice. Combined organic layers were washed with brine solution twice. The organic layer was concentrated and column chromatography of the crude product on silica gel, using 30% EtOAC in hexane as eluent, gave pure Baylis-Hillman adduct in 97% yield (2.47 g).

Workup

  1. customreaction progress
  2. customwas removed under reduced pressure
  3. washwashed with water
  4. extractionextracted with CHCl3 thrice
  5. washCombined organic layers were washed with brine solution twice
  6. concentrationThe organic layer was concentrated
  7. customgave pure Baylis-Hillman adduct in 97% yield (2.47 g)

Sources & evidence

ORD record
ord-a26340e2a3c941729c95c0fdf97fa665
Source dataset
uspto-grants-2010_02
Patent number
US07666883B2

Reaction notes

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