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

HRID 1418017Notes

Reaction equation

[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]

Participants

Conditions

Temperature: -78 °C

Procedure

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 (Na2SO4) 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%).

Workup

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)
dry with materialdry (Na2SO4)
custompurify by silica gel chromatography (2.5:1 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-f6fe73c486f745d786b19f72b55e1462
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05880119

Reaction notes

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