Water → 1-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-methyl-1-[4-(4-morpholinyl)phenyl]propan-1-ol

HRID 1743186Notes

Reaction equation

HRID 1743186 reaction equation
C([Li])CCC.Br[C:7]1[C:12]([CH3:13])=[C:11]([O:14][CH3:15])[C:10]([CH3:16])=[C:9]([CH3:17])[C:8]=1[O:18][CH3:19].[CH3:20][CH:21]([CH3:36])[C:22]([C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[CH:26][CH:25]=1)=[O:23].O>O1CCCC1>[CH3:19][O:18][C:8]1[C:9]([CH3:17])=[C:10]([CH3:16])[C:11]([O:14][CH3:15])=[C:12]([CH3:13])[C:7]=1[C:22]([C:24]1[CH:25]=[CH:26][C:27]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)=[CH:28][CH:29]=1)([OH:23])[CH:21]([CH3:36])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 2973651-Bromo-2,5-dimethoxy-3,4,6-trimethylbenzeneHCID 222382912-Methyl-1-[4-(4-morpholinyl)phenyl]-1-propanoneHCID 178418339Butyllithium

Product 1

HCID 222382871-(2,5-Dimethoxy-3,4,6-trimethylphenyl)-2-methyl-1-[4-(4-morpholinyl)phenyl]propan-1-olYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (1.6 M, 18.1 mL, 29.0 mmol) was added to a solution of 1-bromo-2,5-dimethoxy-3,4,6-trimethylbenzene (7.52 g, 29.0 mmol) in tetrahydrofuran (50 mL) at −78° C., and the mixture was stirred for 20 minutes at the same temperature. To the reaction mixture was added 2-methyl-1-[4-(4-morpholinyl)phenyl] propan-1-one (6.15 g, 26.4 mmol), and the mixture was stirred for 30 minutes at room temperature. Water (40 mL) was poured into the reaction mixture, which was then extracted three times with ethyl acetate. The organic layers were combined, washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was crystallized from ethanol to obtain the title compound (8.40 g, yield 90%).

Workup

  1. stirringthe mixture was stirred for 30 minutes at room temperature
  2. extractionwas then extracted three times with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-f4b681dd82b84322b2d06ca9190011ef
Source dataset
uspto-grants-2006_03
Patent number
US07008950B1

Reaction notes

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