Ozone → 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-formyl-phenyl)-propionic acid, 2-trimethylsilanyl-ethyl ester

HRID 2713

Reaktionsgleichung

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]=C)[C:13]([O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[O:14].[O:31]=[O+][O-]>C(Cl)Cl.CO>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]=[O:31])[C:13]([O:15][CH2:16][CH2:17][Si:18]([CH3:19])([CH3:21])[CH3:20])=[O:14]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Dissolve 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-(2-vinyl-phenyl)-propionic acid, 2-trimethylsilanyl-ethyl ester (2.61 g, 6.19 mmol) in methylene chloride (70 mL) and methanol (75 mL). Cool to -78° C. and treat with ozone until a blue color persists. Purge with nitrogen and add dimethylsulfide (7 mL) and pyridine (0.35 mL). Allow to warm to room temperature gradually overnight. Partition between methylene chloride (100 mL) and water (40 mL). Extract the aqueous with methylene chloride (50 mL), dry (Na2 SO4) and purify by silica gel chromatography (2.5:1 hexane/ethyl acetate) to give the title compound as a colorless viscous oil (2.65 g, 100%).

Aufarbeitung

customPurge with nitrogen
additionadd dimethylsulfide (7 mL) and pyridine (0.35 mL)
temperatureAllow to warm to room temperature gradually overnight
customPartition between methylene chloride (100 mL) and water (40 mL)
extractionExtract the aqueous with methylene chloride (50 mL)
customdry (Na2 SO4)
custompurify by silica gel chromatography (2.5:1 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag: ord-d5c09177d7e64c599435165854334fd6
Quelldatensatz: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05731306

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