Phthalimide → HCID 53485842, compound

HRID 720754Notes

Reaction equation

HRID 720754 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.[CH3:12][C:13](C)([O-:15])[CH3:14].[K+].C([C@@H]1OC1)Cl>[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:13]1[O:15][CH2:14]1

Participants

6

Reactant 3

HCID 6809PhthalimideHCID 2734062(-)-EpichlorohydrinHCID 23665647Potassium tert-butoxide

Product 1

HCID 53485842HCID 53485842, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 3776IsopropanolSolvent

Procedure

Into a reaction vessel were put phthalimide (2.00 g, 13.6 mmol), benzyltrimethylammonium chloride (252 mg, 1.36 mol) and isopropanol (25 mL) and the mixture was ice cooled. Thereto were added potassium tert-butoxide (3.05 g, 27.2 mmol) in several divided portions and then (R)-epichlorohydrin (2.52 g, 27.2 mmol). The mixture was reacted at room temperature for 26 hours and then post-treatment was carried out to give crude (R)-glycidylphthalimide (0.45 g, yield 17%, optical purity 96% e.e.) as a yellow highly viscous product.

Workup

  1. customInto a reaction vessel were put
  2. temperaturecooled
  3. customThe mixture was reacted at room temperature for 26 hours

Sources & evidence

ORD record
ord-aa9b4d45dda049f2921619135889275e
Source dataset
uspto-grants-2006_11
Patent number
US07135576B2

Reaction notes

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