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

HRID 1707886Notes

Reaction equation

HRID 1707886 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1.[CH3:13][C:14]([OH:18])([CH3:17])[C:15]#[CH:16]>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>[CH3:13][C:14]([OH:18])([CH3:17])[C:15]#[C:16][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 27355991-Bromo-4-pentylbenzene

Product 1

HCID 189600502-Methyl-4-(4-pentylphenyl)-3-butyn-2-olYield 79.3%

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-pentylbenzene (102 g), 3-methyl-1-butyne-3-ol (38 g), triphenylphosphine (2 g) and bis(triphenylphosphine)palladium(II) chloride (1 g) were dissolved in triethylamine (390 ml) under nitrogen atmosphere, and then copper(I) iodide (0.3 g) was added thereto. After stirring at room temperature for 1 hour, the reaction mixture was further stirred at 90° C. for 5 hours. The resulting precipitated crystals were filtered, and then triethylamine was distilled off therefrom, followed by extracting with chloroform. The resultant was washed twice with 10% hydrochloric acid, and further with water twice, and then chloroform was distilled off therefrom. The residue was purified using silica gel-chloroform column chromatography to give 3-methyl-1-(4'-pentylphenyl)-1-butyne-3-ol (82 g).

Workup

  1. stirringthe reaction mixture was further stirred at 90° C. for 5 hours
  2. customThe resulting precipitated crystals
  3. filtrationwere filtered
  4. distillationtriethylamine was distilled off
  5. extractionby extracting with chloroform
  6. washThe resultant was washed twice with 10% hydrochloric acid
  7. distillationfurther with water twice, and then chloroform was distilled off
  8. customThe residue was purified

Sources & evidence

ORD record
ord-0a40b9eb03e24266b98f33685646c4e5
Source dataset
uspto-grants-1994_10
Patent number
US05356558

Reaction notes

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