Water → HCID 18689382, compound

HRID 1871842Notes

Reaction equation

HRID 1871842 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[O:10][C:11]([CH3:16])([CH3:15])[C:12](=O)[N:13]=2)[CH:6]=[CH:7][CH:8]=1.[CH:17]12[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[C:18]1=O)[CH2:24]2.O.C(OCC)(=O)C>C1COCC1.[Cu].[Zn].[Cl-].[Cl-].[Cl-].[Ti+3]>[CH:17]12[CH2:26][CH:21]3[CH2:22][CH:23]([CH2:25][CH:19]([CH2:20]3)[C:18]1=[C:12]1[C:11]([CH3:16])([CH3:15])[O:10][C:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)=[N:13]1)[CH2:24]2

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 64151AdamantanoneHCID 18689379HCID 18689379, compound

Product 1

HCID 18689382HCID 18689382, compound

Reagents, catalysts & solvents 3

HCID 10290809Zinc copper coupleCatalystHCID 10313229titanium(III) trichlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

122 mmol zinc-copper couple is added to a suspension of 35 mmol titanium trichloride in 60 ml absolute THF while stirring carefully. After heating for one hour under reflux a mixture of 11.4 mmol 2-(3'-methoxyphenyl)-5,5-dimethyl-oxazolin-4-one and 8.1 mmol adamantanone is added after cooling to room temperature. It is heated for 4 h to boiling at reflux. After cooling to room temperature it is poured onto 200 ml water. The mixture is shaken out twice with 200 ml ethyl acetate. The combined organic phases are washed once with water and separated. After drying over sodium sulfate it is filtered and the solvent is removed by distillation. The oily residue is separated by column chromatography (silica gel: ethyl acetate/petroleum ether 1:9).

Workup

  1. temperatureAfter heating for one hour
  2. temperatureunder reflux
  3. additionis added
  4. temperatureIt is heated for 4 h
  5. temperatureat reflux
  6. temperatureAfter cooling to room temperature it
  7. washThe combined organic phases are washed once with water
  8. customseparated
  9. dry with materialAfter drying over sodium sulfate it
  10. filtrationis filtered
  11. customthe solvent is removed by distillation
  12. customThe oily residue is separated by column chromatography (silica gel: ethyl acetate/petroleum ether 1:9)

Sources & evidence

ORD record
ord-f6c2394e6ace45fbb9eafe48221447be
Source dataset
uspto-grants-2000_08
Patent number
US06107036

Reaction notes

Loading…