Phthalimide → HCID 53485842, compound

HRID 720752Notes

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.[CH2:12]([C@@H:14]1[O:16][CH2:15]1)Cl.C(=O)([O-])[O-].[Na+].[Na+].CC(C)([O-])C.[K+]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.C(O)(C)C>[CH2:12]([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:14]1[O:16][CH2:15]1

Participants

Conditions

Temperature: 20 °C

Procedure

Into a reaction vessel were put phthalimide (2.00 g, 13.6 mol), (R)-epichlorohydrin (2.52 g, 27.2 mol), anhydrous sodium carbonate (144 mg, 1.36 mol), benzyltrimethylammonium chloride (252 mg, 1.36 mol) and isopropanol (13 ml) and the mixture was reacted at room temperature for 15 hours. After removal unreacted epichlorohydrin, to the residue was added isopropanol (13 ml) and the mixture is cooled to 20° C. Then thereto was gradually dropped a mixture of potassium tert-butoxide (1.83 g, 16.3 mol) and isopropanol (7 ml) and the mixture was stirred for 1 hour at the same temperature. The solvent was removed and to the residue was added ethyl acetate (13 ml). The mixture was washed with water (7 ml), and then ethyl acetate was removed to give crude (R)-glycidylphthalimide (2.16 g, yield 78%, optical purity 98% e.e.) as white crystals.

Workup

customInto a reaction vessel were put
customAfter removal unreacted epichlorohydrin
additionto the residue was added isopropanol (13 ml)
additionThen thereto was gradually dropped
customThe solvent was removed and to the residue
additionwas added ethyl acetate (13 ml)
washThe mixture was washed with water (7 ml)
customethyl acetate was removed

Sources & evidence

ORD record: ord-78ec456078cb462bb07879c0ed748260
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135576B2

Reaction notes

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