Triphenylphosphine → E-4-(Carbo-tert.-butoxy)-4'-(4-carbo-tert.-butoxystyryl)tolan

HRID 974214Notes

Reaction equation

HRID 974214 reaction equation
[C:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]([CH3:19])(O)[CH3:17])=[CH:10][CH:9]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].BrC1C=[CH:25][C:24]([CH:27]=[CH:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:31][CH:30]=2)=[CH:23]C=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl-].[NH4+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1(C)C=CC=CC=1.[OH-].[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]2[CH:19]=[CH:23][C:24](/[CH:27]=[CH:28]/[C:29]3[CH:30]=[CH:31][C:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:33][CH:34]=3)=[CH:25][CH:17]=2)=[CH:10][CH:9]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

10

Reactant 4

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 199856624-(4-Carbo-tert.-butoxyphenyl)-2-methyl-3-butyn-2-olHCID 573054164-Bromo-4'-carbo-tert.-butoxystilbene

Product 1

HCID 131717083E-4-(Carbo-tert.-butoxy)-4'-(4-carbo-tert.-butoxystyryl)tolan

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 66133Benzyl triethylammonium chlorideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 13.02 g of 4-(4-carbo-tert.-butoxyphenyl)-2-methyl-3-butyn-2-ol, 17.97 g of 4-bromo-4'-carbo-tert.-butoxystilbene, 0.93 g of triphenylphosphine. 0.34 g of benzyltriethylammonium chloride, 175 mg of bis(triphenylphosphine)palladium(II) chloride and 175 mg of copper(I) iodide in 70 ml of toluene and 36 ml of 5,5N NaOH is vigorously stirred under reflux for 48 hours. After the addition of 250 ml of saturated ammonium chloride solution, the reaction product is extracted with methylene chloride, dried and concentrated by evaporation.

Workup

  1. temperatureunder reflux for 48 hours
  2. extractionthe reaction product is extracted with methylene chloride
  3. customdried
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-aa3419491cbf42b1809644366a05a25b
Source dataset
uspto-grants-1991_11
Patent number
US05068300

Reaction notes

Loading…