Oxygen → 2-(p-Octyloxyphenyl)-5-(4-trifluoromethyloctyl)pyridine

HRID 275249Notes

Reaction equation

HRID 275249 reaction equation
C([Li])CCC.[CH2:6]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][N:22]=2)=[CH:17][CH:16]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].C(NC(C)C)(C)C.O=O.[F:37][C:38]([F:48])([F:47])[CH:39]([CH2:43][CH2:44][CH2:45][CH3:46])[CH2:40][CH2:41]I.[Cl-].[NH4+]>CCCCCC.C1COCC1>[CH2:6]([O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][CH2:41][CH2:40][CH:39]([C:38]([F:37])([F:48])[F:47])[CH2:43][CH2:44][CH2:45][CH3:46])=[CH:23][N:22]=2)=[CH:19][CH:20]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

9

Reactant 6

HCID 977OxygenHCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 14766021HCID 14766021, compoundHCID 151000113-Trifluoromethylheptyl iodideHCID 178418339Butyllithium

Product 1

HCID 151000122-(p-Octyloxyphenyl)-5-(4-trifluoromethyloctyl)pyridine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

0.2 mol of a 1.6 N solution of n-butyllithium in hexane and subsequently, at -30° C. to -40° C., a solution of 0.19 mol of 2 (p-octyloxyphenyl)-5-methylpyridine in THF are added to 0.2 mol of diisopropylamine in 100 ml of THF with exclusion of atmospheric oxygen and moisture. The reaction mixture is allowed to warm slowly until a clear solution is produced, and 0.2 mol of 3-trifluoromethylheptyl iodide (optically active) is then added. After 12 hours, the reaction mixture is hydrolyzed using saturated ammonium chloride solution, and is then subjected to customary work-up, giving optically active 2-(p-octyloxyphenyl)-5-(4-trifluoromethyloctyl)pyridine.

Workup

  1. temperatureto warm slowly until a clear solution
  2. customis produced

Sources & evidence

ORD record
ord-4b936cc7fc22494181bdaf919bc0f91e
Source dataset
uspto-grants-1995_02
Patent number
US05393459

Reaction notes

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