Water → 6-Methoxy-2-(4-methoxybenzyl)-2,3-dihydroisoindol-1-one

HRID 1761020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1761020
C1(P(C2C=CC=CC=2)([CH:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[C:11](=[O:20])[N:10]2[CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)=O)C=CC=CC=1.[OH-].[Na+].O>C1COCC1>[CH3:19][O:18][C:14]1[CH:13]=[C:12]2[C:17]([CH2:9][N:10]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[C:11]2=[O:20])=[CH:16][CH:15]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 225942173-(Diphenyl-phosphinoyl)-6-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one

Produkt 1

HCID 114375476-Methoxy-2-(4-methoxybenzyl)-2,3-dihydroisoindol-1-oneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 3-(diphenyl-phosphinoyl)-6-methoxy-2-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one (1.49 g, 3.1 mmol) in THF (40 mL) containing a solution of sodium hydroxide (2.5 M, 12.4 mL, 30.8 mmol) was heated under reflux for 14 h. The solution was then cooled to RT and water (40 mL) added. The mixture was extracted with diethyl ether and the combined organic extracts washed with water and brine. The organic layer was then dried over sodium sulphate, filtered and evaporated. The residue was then purified by chromatography (SiO2, Hexane:Acetone 6:4) to afford the title product (661 mg, 76%) as a light yellow solid. MS m/e=283.2 (M).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 14 h
  3. extractionThe mixture was extracted with diethyl ether
  4. washthe combined organic extracts washed with water and brine
  5. dry with materialThe organic layer was then dried over sodium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was then purified by chromatography (SiO2, Hexane:Acetone 6:4)

Quellen und Nachweise

ORD-Eintrag
ord-cca6b47dfc2346e79177e0aa12b12ba2
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06846832B2

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