2-Azetidinone, 1-(4-methoxyphenyl)-3,3-dimethyl-4-phenyl- → 3,3-dimethyl-4-phenylazetidin-2-one

HRID 341761Notes

Reaction equation

HRID 341761 reaction equation
COC1C=CC([N:9]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11]([CH3:20])([CH3:19])[C:10]2=[O:21])=CC=1>C(#N)C.O>[CH3:19][C:11]1([CH3:20])[CH:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[NH:9][C:10]1=[O:21]

Participants

4

Reactant 1

HCID 110332922-Azetidinone, 1-(4-methoxyphenyl)-3,3-dimethyl-4-phenyl-

Product 1

HCID 27542183,3-dimethyl-4-phenylazetidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 24.4 g of N-(4-methoxy-phenyl)-3,3-dimethyl-4-phenylazetidin-2-one and 16.5 g of lithium 25 perchlorate in a mixture of 500 cm3 of acetonitrile and 50 cm3 of water, is subjected to electrolysis in a unseparated cell, using a graphite anode and a stainless steel grille as cathode and maintaining a constant potential difference of 1.5 V. At the end of the reaction the solution is concentrated to 1/4 of volume. An extraction is made with ethyl acetate and the organic phase is washed with a solution of aqueous sodium sulphite at 10% and then with water; it is dried with sodium sulphate and then evaporated. The raw product is purified on silica gel, using a mixture of ethyl acetate/hexane as eluant in a ratio of 3/7 and 15.4 g of 3,3-dimethyl-4-phenylazetidin-2-one are obtained (yield (98%).

Workup

  1. customAt the end of the reaction the solution
  2. concentrationis concentrated to 1/4 of volume
  3. extractionAn extraction
  4. washthe organic phase is washed with a solution of aqueous sodium sulphite at 10%
  5. dry with materialit is dried with sodium sulphate
  6. customevaporated
  7. customThe raw product is purified on silica gel
  8. additiona mixture of ethyl acetate/hexane as eluant in a ratio of 3/7 and 15.4 g of 3,3-dimethyl-4-phenylazetidin-2-one
  9. customare obtained (
  10. customyield (98%)

Sources & evidence

ORD record
ord-34a33d1dc6ce4e8897e49758b56ed5fa
Source dataset
uspto-grants-1999_01
Patent number
US05856311

Reaction notes

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