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

HRID 1707883Notes

Reaction equation

HRID 1707883 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.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.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 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

1-Bromo-4-propylbenzene (60 g), 3-methyl-1-butyne-3-ol (38 g), triphenylphosphine (1.3 g) and bis(triphenylphosphine)palladium(II) chloride (0.7 g) were dissolved in triethylamine (260 ml) under nitrogen atmosphere, and then copper(I) iodide (0.2 g) was added thereto. The mixture was stirred at room temperature for 1 hour, and then further stirred at 90° C. for 5 hours. The resulting precipitated crystals were filtered, and then triethylamine was distilled off, followed by extraction with chloroform. The resultant was washed twice with 10% hydrochloric acid, and further with water twice, followed by distilling off chloroform therefrom. The residue was purified by the use of silica gel-chloroform column chromatography to give 3-methyl-1-(4'-propylphenyl)-1-butyne-3-ol (37 g).

Workup

  1. stirringfurther stirred at 90° C. for 5 hours
  2. customThe resulting precipitated crystals
  3. filtrationwere filtered
  4. distillationtriethylamine was distilled off
  5. extractionfollowed by extraction with chloroform
  6. washThe resultant was washed twice with 10% hydrochloric acid
  7. distillationby distilling off chloroform
  8. customThe residue was purified by the use of silica gel-chloroform column chromatography

Sources & evidence

ORD record
ord-8e4c6e78ba884704827227ac582d7373
Source dataset
uspto-grants-1994_10
Patent number
US05356558

Reaction notes

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