Ammonium Chloride → HCID 18001067, compound

HRID 1870436Notes

Reaction equation

HRID 1870436 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=3)=[C:9](OC)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:22]([Mg]Br)[CH2:23][CH3:24].[Cl-].[NH4+]>O1CCCC1>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[O:14][CH2:15][C:16]([CH3:19])([CH3:18])[N:17]=3)=[C:9]([CH2:22][CH2:23][CH3:24])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 18001050HCID 18001050, compoundHCID 178455851HCID 178455851, compound

Product 1

HCID 18001067HCID 18001067, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-(4-Phenyl-2-methoxyphenyl)-4,4-dimethyl-2-oxazoline (3.00 g) is dissolved in tetrahydrofuran (30 ml) under argon atmosphere, and the mixture is stirred with cooling over an ice-bath. To the mixture is added dropwise gradually an about 2M solution of 1-n-propylmagnesium bromide in tetrahydrofuran (8.0 ml) at the same temperature. After addition, the mixture is warmed to room temperature, and stirred for 16 hours. The reaction solution is stirred with cooling over an ice-bath, and thereto is added a saturated aqueous ammonium chloride solution (30 ml). The mixture is warmed to room temperature, and the organic layer is collected. The aqueous layer is extracted with ethyl acetate (30 ml×2), and the extract is combined with the organic layer, washed with a saturated aqueous sodium chloride solution (100 ml×2), dried over magnesium sulfate, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; dichloromethane:n-hexane=1:2→1:1), and evaporated to remove the solvent to give 2-(4-phenyl-2-n-propylphenyl)-4,4-dimethyl-2-oxazoline (2.81 g) as colorless transparent viscous oil.

Workup

  1. temperaturewith cooling over an ice-bath
  2. additionAfter addition
  3. stirringstirred for 16 hours
  4. stirringThe reaction solution is stirred
  5. temperaturewith cooling over an ice-bath
  6. temperatureThe mixture is warmed to room temperature
  7. customthe organic layer is collected
  8. extractionThe aqueous layer is extracted with ethyl acetate (30 ml×2)
  9. washwashed with a saturated aqueous sodium chloride solution (100 ml×2)
  10. dry with materialdried over magnesium sulfate
  11. customevaporated
  12. customto remove the solvent
  13. customThe residue is purified by silica gel column chromatography (solvent; dichloromethane:n-hexane=1:2→1:1)
  14. customevaporated
  15. customto remove the solvent

Sources & evidence

ORD record
ord-6d98937195b44620ac9d447e2d43d748
Source dataset
uspto-grants-2000_08
Patent number
US06096735

Reaction notes

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