Hydrochloric Acid → HCID 131733972, compound

HRID 710954Notes

Reaction equation

HRID 710954 reaction equation
[OH:1][CH2:2][CH2:3][O:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].N1C=CN=C1.Cl[Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24].Cl>C(Cl)Cl>[CH:23]([Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[O:1][CH2:2][CH2:3][O:4][N:5]1[C:6](=[O:15])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:13]1=[O:14])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 10679822HCID 10679822, compound

Product 1

HCID 131733972HCID 131733972, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-hydroxyethoxyl)isoindoline-1,3-dione (622 mg, 3.00 mmol) in dehydrated methylene chloride (6 mL), imidazole (306 mg) and chlorotriisopropylsilane (TIPSCl, 963 μL) were added under an argon atmosphere at room temperature. After the reaction mixture was stirred at room temperature overnight, 2M hydrochloric acid was added to stop the reaction, followed by distilling off methylene chloride under reduced pressure. The resulting aqueous layer was extracted with ethyl acetate, followed by washing the organic layer with saturated brine and then drying over magnesium sulfate. The resulting residue was subjected to silica gel column chromatography (hexane/ethyl acetate=9/1→2/1) to afford 1.04 g of the title compound (yield 95%).

Workup

  1. customthe reaction
  2. distillationby distilling off methylene chloride under reduced pressure
  3. extractionThe resulting aqueous layer was extracted with ethyl acetate
  4. washby washing the organic layer with saturated brine
  5. dry with materialdrying over magnesium sulfate

Sources & evidence

ORD record
ord-042f154483c54c3388ee3eae0ab9d4b9
Source dataset
uspto-grants-2015_11
Patent number
US09181250B2

Reaction notes

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