Hydrochloric Acid → HCID 13693404, compound

HRID 846232Notes

Reaction equation

HRID 846232 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:24])[CH2:22][CH3:23])=[CH:17][CH:16]=1.Br[CH2:26][C:27]([O:29][CH3:30])=[O:28].Cl>C1COCC1.O>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:24])[CH:22]([CH3:23])[CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 60984Methyl bromoacetateHCID 671444-PropanoylanisoleHCID 178418339Butyllithium

Product 1

HCID 13693404HCID 13693404, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of diisopropylamine (5.1 ml) in anhydrous THF (90 ml) at 0° C. is treated under N2 atmosphere with n-butyllithium (1.6 M, 22 ml) for 20 minutes. The mixture was cooled to -78° C., and a solution of 1(4-methoxyphenyl)-1-oxopropane (5 g) in anhydrous THF (40 ml) is added. The mixture was stirred 30 minutes at -78° C., then methyl bromoacetate (3.05 ml) was added dropwise and then mixture was warmed to ambient temperature over 2 hours. After stirring 18 hours at room temperature the mixture was Poured onto ice, water and conc. HCl (3 ml) was added and the solution was extracted with dichloromethane. The organic extracts were washed with brine, dried over N2SO4 and concentrated to an oil which was purified by chromatography on silica gel to provide the title compound as an oil.

Workup

  1. temperaturemixture was warmed to ambient temperature over 2 hours
  2. stirringAfter stirring 18 hours at room temperature the mixture
  3. additionwas added
  4. extractionthe solution was extracted with dichloromethane
  5. washThe organic extracts were washed with brine
  6. customdried over N2SO4
  7. concentrationconcentrated to an oil which
  8. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9f7bd6f11828410e89c0918a1d5a1c9f
Source dataset
uspto-grants-1992_08
Patent number
US05135940

Reaction notes

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