Pyridine → HCID 178445656, compound

HRID 2256778Notes

Reaction equation

HRID 2256778 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CN(C)C=O.N1C=CC=CC=1.[CH2:20]([C@H:24]1[CH2:29][CH2:28][C@H:27]([C:30](Cl)=[O:31])[CH2:26][CH2:25]1)[CH2:21][CH2:22][CH3:23]>O>[CH2:20]([C@H:24]1[CH2:25][CH2:26][C@H:27]([C:30]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=2)=[O:31])[CH2:28][CH2:29]1)[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 78084-BromophenolHCID 178445654HCID 178445654, compound

Product 1

HCID 178445656HCID 178445656, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

26 g of 4-bromophenol, 100 ml of dimethylformamide, and 13 g of pyridine were dissolved. 31 g of commercially available trans-4-n-butylcyclohexane carboxylic acid chloride was added dropwise to the solution and the mixture was heated while stirring. The reaction mixture was poured into water to produce crystals. The crystals were collected by filtration, washed with dilute HCl and then water, dried in vacuum, and recrystallized from a mixed solvent of ethyl acetate and methanol to obtain 44 g of 4-bromophenyl trans-4-n-butylcyclohexane carboxylate. To this were added 20 g of 4-ethoxyphenyl acetylene, 0.09 g of bis(triphenylphosphine)-palladium(II) chloride, 0.1 g of copper iodide, 0.79 g of triphenylphosphine, and 260 ml of triethylamine, and the mixture was heated while stirring. After the reaction, the reaction product was poured into water and neutralized with HCl to produce crystals. The crystals were collected by filtration, washed with water, dried in vacuum, and recrystallized from a mixed solvent of ethyl acetate and methanol to obtain 40 g of a compound having the following formula. ##STR43##

Workup

  1. temperaturethe mixture was heated
  2. customto produce crystals
  3. filtrationThe crystals were collected by filtration
  4. washwashed with dilute HCl
  5. dry with materialwater, dried in vacuum
  6. customrecrystallized from a mixed solvent of ethyl acetate and methanol

Sources & evidence

ORD record
ord-9ceb95e0b2a64d25a2d67646c51d71ce
Source dataset
uspto-grants-1997_08
Patent number
US05656198

Reaction notes

Loading…