Diisopropylamine → 4-[2-(3,5-Difluoro-4-propylphenyl)ethyl]-4'-pentyl-1,1'-biphenyl

HRID 257683Notes

Reaction equation

HRID 257683 reaction equation
C([N-][CH:5]([CH3:7])[CH3:6])(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[CH2:21]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]3[CH:45]=[C:44]([F:46])[CH:43]=[C:42]([F:47])[CH:41]=3)=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)[CH2:22][CH2:23][CH2:24][CH3:25].CC1N(C(N(C)C)=O)C1.ICCC>C1COCC1.CCCCCC.C1COCC1.CCCCCC.O>[CH2:21]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][C:40]3[CH:41]=[C:42]([F:47])[C:43]([CH2:7][CH2:5][CH3:6])=[C:44]([F:46])[CH:45]=3)=[CH:34][CH:33]=2)=[CH:28][CH:27]=1)[CH2:22][CH2:23][CH2:24][CH3:25]

Participants

11

Reactant 6

HCID 7912DiisopropylamineHCID 336431-IodopropaneHCID 2724682Lithium diisopropylamideHCID 11007919N,N,2-trimethylaziridine-1-carboxamideHCID 157248231-(4'-Pentylbiphenyl-4-yl)-2-(3,5-difluorophenyl)ethaneHCID 178418339Butyllithium

Product 1

HCID 197837004-[2-(3,5-Difluoro-4-propylphenyl)ethyl]-4'-pentyl-1,1'-biphenyl

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 21883165Tetrahydrofuran hexaneSolvent

Procedure

A solution of lithium diisopropylamide (0.02 mol) in THF/hexane, prepared from 0.02 mol of diisopropylamine in 25 ml of THF and 12.5 ml of a 1.6-molar solution of n-butyllithium in hexane, is added dropwise at 25° C. to a mixture of 0.02 mol of 1-(4'-pentylbiphenyl-4-yl)-2-(3,5-difluorophenyl)ethane, 0.02 mol of N,N-dimethylpropyleneurea, 0.02 mol of 1-iodopropane and 25 ml of THF. After stirring at room temperature for 1.5 hours, the reaction mixture is poured into water, the phases are separated, and the aqueous phase is extracted with 2×50 ml of methylene chloride. Drying over magnesium sulfate, evaporation of the solvent and chromatography give the pure product.

Workup

  1. customthe phases are separated
  2. extractionthe aqueous phase is extracted with 2×50 ml of methylene chloride
  3. dry with materialDrying over magnesium sulfate, evaporation of the solvent and chromatography
  4. customgive the pure product

Sources & evidence

ORD record
ord-c069cc17e4664a2fa4e6d624e4865cd8
Source dataset
uspto-grants-1993_11
Patent number
US05262556

Reaction notes

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