Propargyl alcohol → 3-Phenyl-2-propyn-1-ol

HRID 2059238Notes

Reaction equation

HRID 2059238 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:8]#[C:9][CH2:10][OH:11].C(NCC)C.BrC1C=CC=CN=1>[Cu]I.C(OCC)C>[C:2]1([C:8]#[C:9][CH2:10][OH:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7859Propargyl alcoholHCID 7961BromobenzeneHCID 79732-BromopyridineHCID 8021Diethylamine

Product 1

HCID 1231153-Phenyl-2-propyn-1-ol

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 0.7 g (1 mmol) of bis-triphenylphosphinepalladium dichloride and 0.38 g (2 mmols) of copper (I) iodide is added, with stirring, to 31.6 g (200 mmols) of bromobenzene, 16.8 g (300 mmols) of 1-propyn-3-ol and 300 ml of diethylamine. The reaction mixture is stirred in an argon atmosphere at room temperature (20°-25° C.), and within one hour the mixture heats up to about 30° C. A precipitate commences to occur, and after a reaction time of 6 hours, no further bromopyridine can be detected according to chromatographic analysis. 200 ml of diethyl ether are added to the reaction mixture and this is then filtered. The filtrate is washed with 200 ml of water, dried over magnesium sulfate, and concentrated by evaporation to leave a solid residue. Recrystallisation from diethyl ether yields 1-(phenyl)-propyn-3-ol. 1H-NMR Spectrum 100 MHz (CDCl3, TMS) δ in ppm: 2.4(s); 4.5(s); 7.2-7.5(m) in the ratio of 1:2:5.

Workup

  1. additionis added
  2. customafter a reaction time of 6 hours
  3. filtrationthis is then filtered
  4. washThe filtrate is washed with 200 ml of water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated by evaporation
  7. customto leave a solid residue
  8. customRecrystallisation from diethyl ether

Sources & evidence

ORD record
ord-d782d0742d88483e9af8e08b6add48c1
Source dataset
uspto-grants-1982_03
Patent number
US04322432

Reaction notes

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