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

HRID 566719노트

반응식

HRID 566719 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-44c969fb23e842dabeb9579cb11af323
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06174901B1

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