Triethylamine → HCID 20481557, compound

HRID 1648725Notes

Reaction equation

HRID 1648725 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10](O)([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[OH-:14].[K+].P([C:29]1[CH:34]=[CH:33]C=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:35]([N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])[CH3:36]>CCOCC.[Pd].[Cu]I>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:12]=[CH:33][C:34]([O:14][CH2:36][CH2:35][N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])=[CH:29][CH:11]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 14797Potassium HydroxideHCID 51637444-(4-fluorophenyl)-2-methylbut-3-yn-2-ol

Product 1

HCID 20481557HCID 20481557, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 25.2 g (0.1 mole) of 1-4-(bromophenoxy)-2-diethylaminoethane and 17.8 g (0.1 mole) of 1-fluoro-4-(3-hydroxy-3-methyl-1-butyn-1-yl)benzene in 250 ml of triethylamine are added, under nitrogen, 11.2 g of pulverised potassium hydroxide, 0.7 g of the palladium complex PdCl2 [P(C6H5)3 ]2 and 0.13 g of copper(I) iodide. The reaction mixture is subsequently stirred for 14 hours at 80° C. The reaction mixture is taken up in 250 ml of ether and the solution is washed twice with 100 ml of water and 100 ml of aqueous K2CO3 solution, treated with activated charcoal and evaporated to dryness. Vacuum distillation of the residue yields 9.5 g (33%) of 1-[4-(4-fluorophenylethynyl)phenoxy]-2-diethylaminoethane with a boiling point of 156°-162° C./0.08 mb.

Workup

  1. washthe solution is washed twice with 100 ml of water and 100 ml of aqueous K2CO3 solution
  2. additiontreated with activated charcoal
  3. customevaporated to dryness
  4. distillationVacuum distillation of the residue

Sources & evidence

ORD record
ord-f86f97f87ec243c29694bfca34829621
Source dataset
uspto-grants-1983_11
Patent number
US04412856

Reaction notes

Loading…