2-Methyl-3-butyn-2-ol → 4-(4-Cyanophenyl)-2-methyl-3-butyne-2-ol

HRID 1707889Notes

Reaction equation

HRID 1707889 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][C:11]([OH:15])([CH3:14])[C:12]#[CH:13]>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>[CH3:10][C:11]([OH:15])([CH3:14])[C:12]#[C:13][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 82582-Methyl-3-butyn-2-olHCID 12162Benzonitrile, 4-bromo-

Product 1

HCID 28221554-(4-Cyanophenyl)-2-methyl-3-butyne-2-olYield 79.6%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

4-Bromobenzonitrile (30 g), 3-methyl-1-butyne-3-ol (13.4 g), triphenylphosphine (0.7 g) and bis(triphenylphosphine)palladium(II) chloride (0.3 g) were dissolved in triethylamine (140 ml) under nitrogen atmosphere, and then copper(I) iodide (0.1 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 distilled under reduced pressure (140° to 160° C./5 mmHg) to give 3-methyl-1-(4'-cyanophenyl)-1-butyne-3-ol (23.5 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. distillationThe residue was distilled under reduced pressure (140° to 160° C./5 mmHg)

Sources & evidence

ORD record
ord-6f64f0fd54944f2c83d704e10dfacb4a
Source dataset
uspto-grants-1994_10
Patent number
US05356558

Reaction notes

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