Water → 6-Methoxy-2,3-dihydro-1H-isoindol-1-one

HRID 1761021ノート

反応式

HRID 1761021 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][N:8](CC3C=CC(OC)=CC=3)[C:9]2=[O:12])=[CH:5][CH:4]=1.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[Ce].O>C(#N)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][NH:8][C:9]2=[O:12])=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 962Water2 回HCID 407333Cerate(2-), hexakis(nitrato-kappaO)-, potassium (1:2), (OC-6-11)-HCID 114375476-Methoxy-2-(4-methoxybenzyl)-2,3-dihydroisoindol-1-one

生成物 1

HCID 140056236-Methoxy-2,3-dihydro-1H-isoindol-1-one収率 43%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 6-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one (300 mg, 1.1 mmol) and ammonium ceric nitrate (2.2 g, 4.0 mmol) in acetonitrile:water (12 mL, 2:1) was stirred at RT for 1 h. Then the mixture was poured into water and extracted with ethyl acetate. The combined extracts were then washed with sodium hydrogen carbonate and water. The organic layer was then dried over sodium sulphate, filtered and evaporated. The residue was then purified by chromatography (SiO2, dichloromethane:MeOH 20:1) to afford the title product (75 mg, 43%) as a light yellow solid. MS m/e=164.2 (M).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined extracts were then washed with sodium hydrogen carbonate and water
  3. dry with materialThe organic layer was then dried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was then purified by chromatography (SiO2, dichloromethane:MeOH 20:1)

出典と根拠

ORDレコード
ord-d0a10769b8b847289082a14e60c453a1
出典データセット
uspto-grants-2005_01
特許番号
US06846832B2

反応ノート

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