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

HRID 566719ノート

反応式

HRID 566719 の反応式
[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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-44c969fb23e842dabeb9579cb11af323
出典データセット
uspto-grants-2001_01
特許番号
US06174901B1

反応ノート

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