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

HRID 1761022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1761022
[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

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 62406Trifluoromethanesulfonic acidHCID 516892Sodium BicarbonateHCID 114375476-Methoxy-2-(4-methoxybenzyl)-2,3-dihydroisoindol-1-one

Produkt 1

HCID 140056236-Methoxy-2,3-dihydro-1H-isoindol-1-oneAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-6649b023f8594aafb07cd2645c2f598a
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06846832B2

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