HCID 178418546, compound → HCID 178445611, compound

HRID 2254945Notes

Reaction equation

HRID 2254945 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH:11]([CH2:14][CH2:15][C@H:16]3[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:17]3)[CH2:10][O:9]2)=[CH:4][C:3]=1[F:26].[C:27]([Cu])#[N:28]>CN1C(=O)CCC1>[C:27]([C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:13][CH2:12][C@H:11]([CH2:14][CH2:15][C@H:16]3[CH2:21][CH2:20][C@H:19]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:18][CH2:17]3)[CH2:10][O:9]2)=[CH:4][C:3]=1[F:26])#[N:28]

Participants

4

Reactant 2

HCID 178418546HCID 178418546, compoundHCID 178445608HCID 178445608, compound

Product 1

HCID 178445611HCID 178445611, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

8.4 g (0.02 mol) of 2-(4'-bromo-3'-fluorophenyl)-5-[2'-(trans-4"-butylcyclohexyl)ethyl]-1,3-dioxane and 2.7 g (0.03 mol) of CuCN were refluxed in 100 cm3 of NMP for 2 hours. The product was cooled to room temperature and 4 cm3 of EDA was added. The solution was poured into 100 cm3 of ice water, extracted with hexane, and washed with an aqueous solution of EDA and water. The hexane was distilled off. The residue was treated through a silica gel column with chloroform as the solvent and the chloroform was distilled off. The residue was recrystallized from a solvent mixture of acetone and methanol to yield 3.1 g (0.008 mol) of trans-2-(4'-cyano-3'fluorophenyl)-5-[2'-(trans-4"-butylcyclohexyl)ethyl]-1,3-dioxane. The phase transition points of this compound, measured by DSC, were: ##STR49## wherein C is the crystal phase, N is the nematic phase, and I is the isotropic liquid phase.

Workup

  1. addition4 cm3 of EDA was added
  2. extractionextracted with hexane
  3. washwashed with an aqueous solution of EDA and water
  4. distillationThe hexane was distilled off
  5. additionThe residue was treated through a silica gel column with chloroform as the solvent
  6. distillationthe chloroform was distilled off
  7. customThe residue was recrystallized from a solvent mixture of acetone and methanol

Sources & evidence

ORD record
ord-6a1a27c170bf411682ac82f6b24d5a8f
Source dataset
uspto-grants-1993_08
Patent number
US05238599

Reaction notes

Loading…