Propargyl alcohol → 3-(Furan-3-yl)prop-2-yn-1-ol

HRID 1780912Notes

Reaction equation

HRID 1780912 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][CH:3]=1.[CH2:7]([OH:10])[C:8]#[CH:9]>[Cu]I>[O:4]1[CH:5]=[CH:6][C:2]([C:9]#[C:8][CH2:7][OH:10])=[CH:3]1

Participants

4

Reactant 2

HCID 7859Propargyl alcoholHCID 891643-Bromofuran

Product 1

HCID 227309543-(Furan-3-yl)prop-2-yn-1-ol

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

To a mixture of 3-bromofuran (10 g, 0.068 mol) and propargyl alcohol (4.3 ml, 0.074 mol) in 200 ml of TEA was added under argon, CuI (0.26 g, 1.4 mmol) and [(C6H5)3P]2PdCl2 (1.05 g, 1.4 mmol) and the mixture was stirred at 0° C. for 2 hours and at room temperature for 72 hours. The reaction mixture was cooled, decanted, and the solid was washed with TEA. The combined TEA solution was concentrated in vacuo and the residue was distilled (Kugelrohr distillation) to afford 1.48 g (17.8%) of 3-(3-furyl-2-propynyl alcohol.

Workup

  1. additionwas added under argon
  2. temperatureThe reaction mixture was cooled
  3. customdecanted
  4. washthe solid was washed with TEA
  5. concentrationThe combined TEA solution was concentrated in vacuo
  6. distillationthe residue was distilled
  7. distillation(Kugelrohr distillation)

Sources & evidence

ORD record
ord-6ce3346cf8114cf58cd9e465b5199dfe
Source dataset
uspto-grants-1997_05
Patent number
US05631264

Reaction notes

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