Water → beta-(4-(4-Propylcyclohexyl)cyclohexyl)-2-trifluoromethyl-3-fluoro-4-ethoxy styrene

HRID 1174447Notes

Reaction equation

HRID 1174447 reaction equation
[CH2:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH:10]2[CH2:15][CH2:14][CH:13]([CH:16]=[CH:17][C:18]3[CH:23]=[C:22]([Si](C)(C)C)[C:21]([O:28][CH2:29][CH3:30])=[C:20]([F:31])[C:19]=3[C:32]([F:35])([F:34])[F:33])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].O>C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[CH2:1]([CH:4]1[CH2:5][CH2:6][CH:7]([CH:10]2[CH2:11][CH2:12][CH:13]([CH:16]=[CH:17][C:18]3[CH:23]=[CH:22][C:21]([O:28][CH2:29][CH3:30])=[C:20]([F:31])[C:19]=3[C:32]([F:35])([F:33])[F:34])[CH2:14][CH2:15]2)[CH2:8][CH2:9]1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 962WaterHCID 86614748beta-(4-(4-Propylcyclohexyl)cyclohexyl)-2-trifluoromethyl-3-fluoro-4-ethoxy-5-trimethylsilyl styrene

Product 1

HCID 67058734beta-(4-(4-Propylcyclohexyl)cyclohexyl)-2-trifluoromethyl-3-fluoro-4-ethoxy styrene

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 11078149TBAF tetrahydrofuranSolvent

Procedure

16.03 g of crude of β-(4-(4-propylcyclohexyl)cyclohexyl)-2-trifluoromethyl-3-fluoro-4-ethoxy-5-trimethylsilyl styrene was dissolved in 35 mL of THF, to which 23.4 mL of tetrabutyl ammonium fluoride/THF solution (1 mol/L) was dropped and stirred for 2 hours. The reaction solution was poured into 100 ml of water and extracted with 200 ml of toluene. The organic layer was washed with 100 ml of an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The residue was purified by silica gel column chromatography (eluent: heptane/toluene=8/2) and further recrystallized twice from a heptane/ethanol mixed solvent to obtain 7.89 g of β-(4-(4-propylcyclohexyl)cyclohexyl)-2-trifluoromethyl-3-fluoro-4-ethoxy styrene. The compound showed a liquid crystal phase and the transition points were as shown below.

Workup

  1. additionwas dropped
  2. extractionextracted with 200 ml of toluene
  3. washThe organic layer was washed with 100 ml of an aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue was purified by silica gel column chromatography (eluent: heptane/toluene=8/2)
  6. customfurther recrystallized twice from a heptane/ethanol mixed solvent

Sources & evidence

ORD record
ord-c0e4cd7766c646cd83f2f40fabf11b85
Source dataset
uspto-grants-2010_11
Patent number
US07838087B2

Reaction notes

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