(-)-Epichlorohydrin → HCID 53485842, compound

HRID 720750Notes

Reaction equation

HRID 720750 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH2:13]([C@@H:15]1[O:17][CH2:16]1)Cl>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.CN(C=O)C>[CH2:13]([C:10]1[CH:9]=[CH:8][CH:7]=[C:3]2[C:4]([NH:5][C:1](=[O:11])[C:2]=12)=[O:6])[C@H:15]1[O:17][CH2:16]1

Participants

5

Reactant 2

HCID 2734062(-)-EpichlorohydrinHCID 24194345Phthalimide potassium salt

Product 1

HCID 53485842HCID 53485842, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 6228DimethylformamideSolvent

Procedure

Into a reaction vessel were put potassium phthalimide (5.00 g, 27.0 mmol), benzyltrimethylammonium chloride (0.50 g, 2.70 mmol) and DMF (50 ml) and then thereto was added (R)-epichlorohydrin (5.00 g, 54.0 mmol). The mixture was stirred at room temperature for 16 hours and the solvent was removed. To the residue was added ethyl acetate (30 ml), the mixture was washed with water (20 ml) and ethyl acetate was removed to give crude (R)-glycidylphthalimide (4.48 g, yield: 82%, optical purity: 63% e.e.) as a white solid.

Workup

  1. customInto a reaction vessel were put
  2. customthe solvent was removed
  3. additionTo the residue was added ethyl acetate (30 ml)
  4. washthe mixture was washed with water (20 ml) and ethyl acetate
  5. customwas removed

Sources & evidence

ORD record
ord-c8ab02ddd9c942c7a20200dba28baf31
Source dataset
uspto-grants-2006_11
Patent number
US07135576B2

Reaction notes

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