Methyl iodide → 1,1-Diphenylpropane

HRID 1780038Notes

Reaction equation

HRID 1780038 reaction equation
C(CN[CH2:7][CH2:8][CH:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(OC)=O.C(=O)([O-])[O-].[K+].[K+].CI.C(OCC)(=O)C>CN(C)C=O.O>[C:10]1([CH:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:8][CH3:7])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 86750815HCID 86750815, compound

Product 1

HCID 737261,1-Diphenylpropane

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S)-1-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-2-(N-(carbomethoxy)methylamino-3,3-diphenylpropane (7.6 g, prepared as an intermediate in Example 57) in dimethylformamide (80 ml) was added potassium carbonate (10 g) and methyl iodide (4.5 ml) and the solution stirred in an enclosed atmosphere for 16 hours. Ethyl acetate (200 ml) and water were added and the organic phase washed with water, brine and dried (MgSO4). Purification by silica gel chromatography gave (2S)-1-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-2-((N-(carbomethoxy)methyl)-N-methyl)amino)-3,3-diphenylpropane.

Workup

  1. washthe organic phase washed with water, brine
  2. dry with materialdried (MgSO4)
  3. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-020de54f36c54f2cb3d33ee9a70c78be
Source dataset
uspto-grants-1997_05
Patent number
US05629347

Reaction notes

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