Water → Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate

HRID 439736Notes

Reaction equation

HRID 439736 reaction equation
[C:1]1([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:23](=[N:29][OH:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25].O>CCOCC>[C:1]1([C:7]2([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[O:30][N:29]=[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 107401,1-DiphenylethyleneHCID 6816376Ethyl chloro(hydroximino)acetate

Product 1

HCID 6451155Ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

13.52 g (0.075 mol) of 1,1-diphenylethene and 5.06 g (0.05 mol) of triethylamine are dissolved in 200 ml of ether at 0° C., and 7.58 g (0.05 mol) of ethyl 2-chloro-2-hydroximinoacetate, dissolved in 100 ml of ether, are subsequently added dropwise in the course of approximately two hours. After stirring has been continued for one hour at room temperature, 100 ml of H2O are added, and the mixture is subsequently extracted using ether. After drying over a MgSO4, the ether is distilled off and the residue is purified over a silica gel column (eluent: n-heptane:ethyl acetate=8:2). In this way, 12.7 g (86% of theory) of product of melting point 78° to 81° C. are obtained.

Workup

  1. additionare subsequently added dropwise in the course of approximately two hours
  2. extractionthe mixture is subsequently extracted
  3. dry with materialAfter drying over a MgSO4
  4. distillationthe ether is distilled off
  5. customthe residue is purified over a silica gel column (eluent: n-heptane:ethyl acetate=8:2)
  6. customIn this way, 12.7 g (86% of theory) of product of melting point 78° to 81° C. are obtained

Sources & evidence

ORD record
ord-6e5d0458f33146dc89aa9bbcaaec6c49
Source dataset
uspto-grants-1996_05
Patent number
US05516750

Reaction notes

Loading…