Sodium Hydroxide → HCID 68018990, compound

HRID 1396666Notes

Reaction equation

HRID 1396666 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][N:7](C(OC(C)(C)C)=O)[CH2:8]2.C(OCC)(=O)C.Cl.[OH-].[Na+]>C(OCC)(=O)C>[CH3:1][O:2][CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][NH:7][CH2:8]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 86701154HCID 86701154, compound

Product 1

HCID 68018990HCID 68018990, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 200 mg of tert-butyl 4-(methoxymethyl)-1,3-dihydro-2H-isoindole-2-carboxylate in 2 mL of ethyl acetate was added 2.3 mL of a 4 M hydrogen chloride-ethyl acetate solution under ice-cooling, followed by stirring at room temperature overnight. Under ice-cooling, to the reaction mixture was added a 1 M aqueous sodium hydroxide solution to adjust the pH to about 7. The aqueous layer was separated, the organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 100 mg of 4-(methoxymethyl)isoindoline as a brown oil.

Workup

  1. temperaturecooling
  2. temperatureUnder ice-cooling, to the reaction mixture
  3. customThe aqueous layer was separated
  4. washthe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7162ae68311842c1aebf9e1db0883205
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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