2-Methyl-3-butyn-2-ol → 2-Methyl-4-(4-propylphenyl)-3-butyn-2-ol

HRID 1755619Notes

Reaction equation

HRID 1755619 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH3:10])=[CH:4][CH:3]=1.[CH3:11][C:12]([OH:16])([CH3:15])[C:13]#[CH:14]>C(N(CC)CC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:11][C:12]([OH:16])([CH3:15])[C:13]#[C:14][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 1363741-Bromo-4-propylbenzene

Product 1

HCID 152397712-Methyl-4-(4-propylphenyl)-3-butyn-2-olYield 60.7%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
90 °C

Procedure

60 g of 1-bromo-4-propylbenzene, 38 g of 3-methyl-1-butyn-3-ol, 1.3 g of triphenylphosphine and 0.7 g of bis(triphenylphosphine) palladium(II) chloride were dissolved in 260 ml of triethylamine in nitrogen atmosphere, and 0.2 g of copper(I) iodide was added thereto. This was stirred for one hour at room temperature and for 5 hours at 90° C. The crystals as precipitated were filtered out and, after triethylamine was removed by distillation, extracted with chloroform. These were washed two times with 10% hydrochloric acid and two times with water, and chloroform was removed by distillation. The residue was purified by silicagel-chloroform column chromatography to obtain 37 g of 3-methyl-1-(4'-propylphenyl)-1-butyn-3-ol.

Workup

  1. additionwas added
  2. customThe crystals as precipitated
  3. filtrationwere filtered out
  4. customafter triethylamine was removed by distillation
  5. extractionextracted with chloroform
  6. washThese were washed two times with 10% hydrochloric acid and two times with water, and chloroform
  7. customwas removed by distillation
  8. customThe residue was purified by silicagel-chloroform column chromatography

Sources & evidence

ORD record
ord-c880284c9260465195459b75c8e0163d
Source dataset
uspto-grants-1995_08
Patent number
US05437815

Reaction notes

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