Acetonitrile → HCID 178421665, 화합물

HRID 1737146노트

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HRID 1737146 반응식
[OH:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.S(O[O-])([O-])(=O)=O.[NH4+].[NH4+].[C:22](#N)[CH3:23]>O.C(OCC)C.[N+]([O-])([O-])=O.[Ag+]>[OH:1][C:2]1[C:3](=[O:13])[C:4]2[C:9]([C:10](=[O:12])[C:11]=1[C:22]1([CH3:23])[CH2:10][CH2:11][CH2:2][CH2:3]1)=[CH:8][CH:7]=[CH:6][CH:5]=2

참가 물질

7

반응물 3

HCID 6342AcetonitrileHCID 9855511Ammonium peroxysulphateHCID 178516607HCID 178516607, 화합물

생성물 1

HCID 178421665HCID 178421665, 화합물

시약·촉매·용매 3

HCID 24470Silver Nitrate촉매HCID 962Water용매2회HCID 3283Diethyl Ether용매

반응 조건

온도
20 °C

실험 절차

A 50% excess of this acid was added to a stirred solution of 2-hydroxynaphthalene-1,4-dione (1.00 g, 5.7 mmol), and silver nitrate (600 mg) in a mixture of acetonitrile (20 ml) and water (20 ml) at 65° C. and a solution of ammonium peroxysulphate (1.96 g, 8.6 mmol) in water (10 ml) was slowly added to that over a period of 15 minutes. The mixture was heated for a further hour before cooling to room temperature (about 20° C.) and diluting with diethyl ether (50 ml). The organic phase was separated and washed successively with 25 water, dilute aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution before drying over magnesium sulphate as set out in Example 3. Filtration and evaporation of the solvent under reduced pressure followed by silica gel column chromatography using 2:1 petrol:diethyl ether as eluant gave 2-hydroxy-3-(1-methylcyclopentyl)naphthalene-1,4-dione (mp 116-118° C.).

후처리

  1. temperatureThe mixture was heated for a further hour
  2. customThe organic phase was separated
  3. washwashed successively with 25 water, dilute aqueous sodium hydrogen carbonate solution, water and saturated sodium chloride solution
  4. dry with materialbefore drying over magnesium sulphate
  5. filtrationFiltration and evaporation of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-6b7f9a07a2384d09985199932e760a08
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962002

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