Imidazole → 2-[(2-Chloro-5-ethylpyridine-3-yl)(hydroxy)methyl]cyclohex-2-ene-1-one

HRID 1445559

Reaction equation

HRID 1445559 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:23])[CH2:22][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:23])[CH2:22][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 135942-Cyclohexen-1-oneHCID 249768452-Chloro-5-ethylpyridine-3-carbaldehyde

Product 1

HCID 588802382-[(2-Chloro-5-ethylpyridine-3-yl)(hydroxy)methyl]cyclohex-2-ene-1-oneYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

The clear solution of 2-Chloro-5-ethylnicotinaldehyde (10 mmol, 1.69 g) and imidazole (10 mmol) in 50 ml. of MeOH was slowly charged with 50 ml. of deionized water. To a stirred homogeneous reaction mixture was added 2-cyclohexen-1-one (10.2 mmol., 1.0 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 95% yield (2.43 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 95% yield (2.43 g)

Sources & evidence

ORD record
ord-0a4e91d6deae4e22a91dcc6a58e6c952
Source dataset
uspto-grants-2010_02
Patent number
US07666883B2

Linked notes

Loading…