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

HRID 2085353Notes

Reaction equation

HRID 2085353 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][CH:3]=1.[CH2:7]([OH:10])[C:8]#[CH:9]>C(NC(C)C)(C)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[S:4]1[CH:5]=[CH:6][C:2]([C:9]#[C:8][CH2:7][OH:10])=[CH:3]1

Participants

6

Reactant 2

HCID 7859Propargyl alcoholHCID 133833-Bromothiophene

Product 1

HCID 121814443-(3-thienyl)-2-propyn-1-olYield 48.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 7912DiisopropylamineSolvent2×

Procedure

To a suspension of bis(triphenylphosphine)-palladium (II) chloride (300 mg, 0.42 mmol) and copper (I) iodide (100 mg, 0.50 mmol) in diisopropylamine (100 ml) under nitrogen was added 3-bromothiophene (4.9 g, 30 mmol). After reflux under nitrogen for 1.5 h a solution of propargyl alcohol (3.0 g, 33 mmol) in diisopropylamine (50 ml) was added. After reflux for 5 h the reaction mixture was cooled, filtered and concentrated in vacuo. The residue was submitted to flash chromatography using ether/petroleum ether (1:1) as eluent to give 2 g (48%) of 3-(3-thienyl)-2-propyn-1-ol as a crude product.

Workup

  1. additionwas added
  2. temperatureAfter reflux for 5 h the reaction mixture
  3. temperaturewas cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-289ddc8f6e394ee2ab4f29445f353648
Source dataset
uspto-grants-2004_04
Patent number
US06720342B2

Reaction notes

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