Acetone → 4-Hydroxy-3-pyridine-4-yl-4-m-tolyl-cyclopent-2-en-1-one

HRID 566719Notes

Reaction equation

HRID 566719 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7](=O)[C:8]([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)=[O:9])=[CH:3][CH:2]=1.[OH-].[K+].[CH3:20][C:21]([CH3:23])=[O:22]>>[OH:9][C:8]1([C:10]2[CH:11]=[C:12]([CH3:16])[CH:13]=[CH:14][CH:15]=2)[CH2:23][C:21](=[O:22])[CH:20]=[C:7]1[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 212665371-Pyridine-4-yl-2-m-tolyl-ethane-1,2-dione

Product 1

HCID 212664474-Hydroxy-3-pyridine-4-yl-4-m-tolyl-cyclopent-2-en-1-one

Procedure

To a solution of 1-pyridine-4-yl-2-m-tolyl-ethane-1,2-dione (1.8 g, 8.0 mmole) in acetone (20 mL) was added crushed KOH (448 mg, 8.0 mmole) in one portion at r.t. The reaction mixture was stirred at that temperature for 1 hr before quenching the reaction with aqueous NH4Cl. Standard aqueous work up, followed by chromatographic purification (silica gel, hexane/ethyl acetate) gave the a mixture of the title compound and the regiosiomer, 4-hydroxy-4-pyridine-4-yl-3-m-tolyl-cyclopent-2-en-1-one. MS (m/z): Calcd. C17H15NO2(M+): 265, found (M+H)+: 265.9.

Workup

  1. custombefore quenching
  2. customthe reaction with aqueous NH4Cl
  3. customStandard aqueous work up, followed by chromatographic purification (silica gel, hexane/ethyl acetate)
  4. customgave

Sources & evidence

ORD record
ord-44c969fb23e842dabeb9579cb11af323
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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