Propargyl alcohol → 3-(2-Thienyl)-2-propyn-1-ol

HRID 1108656Notes

Reaction equation

HRID 1108656 reaction equation
I[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[CH2:7]([OH:10])[C:8]#[CH:9]>C(NC(C)C)(C)C.[Cu]I>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:9]#[C:8][CH2:7][OH:10]

Participants

5

Reactant 2

HCID 7859Propargyl alcoholHCID 189212-Iodothiophene

Product 1

HCID 110407693-(2-Thienyl)-2-propyn-1-olYield 73%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 7912DiisopropylamineSolvent2×

Procedure

To a suspension of tetrakis (triphenylphosphine)palladium (300 mg, 0.25 mmol) and copper (I) iodide (100 mg, 0.50 mmol) in diisopropylamine (100 ml) under nitrogen was added 2-iodothiophene (6.3 g, 30 mmol). After stirring 1.5 h at room temperature a solution of propargyl alcohol (3.0 g, 33 mmol) in diisopropylamine (50 ml) was added. After 16 h at room temperature the mixture was filtered and concentrated in vacuo. The residue was submitted to flash chromatography using dichloromethane as eluent to give 3.0 g (73%) of 3-(2-thienyl)-2-propyn-1-ol as a crude product.

Workup

  1. additionwas added
  2. filtrationAfter 16 h at room temperature the mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8982d3322b114b618bd0bac4d197b32a
Source dataset
uspto-grants-2000_05
Patent number
US06069159

Reaction notes

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