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

HRID 1761022ノート

反応式

HRID 1761022 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.C(O)(C(F)(F)F)=O.S(O)(C(F)(F)F)(=O)=O.C(=O)([O-])O.[Na+]>ClCCl.O>[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

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 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 42%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

Alternatively, a mixture of 6-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one (98.5 mg, 0.35 mmol) in dichlormethane (10 mL) containing TFA (1.6 mL, 20.8 mmol) and TfOH (0.6 mL, 7.0 mmol) was heated overnight at 40° C. Then the mixture was poured into sodium hydrogen carbonate and water and the product extracted with dichloromethane. The combined organic layers were 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 (24 mg, 42%) as a light yellow solid. MS m/e=164.2 (M).

後処理

  1. extractionthe product extracted with dichloromethane
  2. dry with materialThe combined organic layers were then dried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was then purified by chromatography (SiO2, dichloromethane:MeOH 20:1)

出典と根拠

ORDレコード
ord-6649b023f8594aafb07cd2645c2f598a
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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