1-Iodonaphthalene → 3-(1-Naphthyl)-2-propyn-1-ol

HRID 1096724Notes

Reaction equation

HRID 1096724 reaction equation
I[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:12]([OH:15])[C:13]#[CH:14].C(N(CC)CC)C>O1CCCC1.[Cu](I)I.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>[C:2]1([C:14]#[C:13][CH2:12][OH:15])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 70041-IodonaphthaleneHCID 7859Propargyl alcoholHCID 8471Triethylamine

Product 1

HCID 114011513-(1-Naphthyl)-2-propyn-1-olYield 49%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

To a stirred solution of de-gassed 1-iodonaphthalene (10.00 g, 39.36 mmol), propargyl alcohol (2.25 g, 40.15 mmol, 1.02 eq.), triethylamine (7.97 g, 78.72 mmol, 2 eq.) and copper iodide (0.02 g, 0.12 mmol, 0.3 mol %) in tetrahydrofuran (30 mL) was added bis(triphenylphosphine)palladium(II) chloride (0.05 g, 0.07 mmol, 0.18 mol %). The mixture was stirred at 35° C. under an atmosphere of nitrogen for 19 h. The mixture was concentrated in vacuo to afford a black tar residue. The residue was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 30%:70%) to afford the desired compound as a yellow oil (3.51 g, 49%). 1H NMR (400 MHz, CDCl3) δ ppm 4.64 (2H, s, CH2), 7.38-7.40 (3H, m, ArH), 7.64 (1H, m, ArH), 7.79 (1H, d, J=8.0 Hz, ArH), 7.81 (1H, d, J 8.0 Hz, ArH), 8.32 (1H, d, J 8.0 Hz, ArH).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto afford a black tar residue
  3. customThe residue was purified by flash chromatography (SiO2, ethyl acetate:petroleum ether 40-60; 30%:70%)

Sources & evidence

ORD record
ord-91e621af4e044509aeb61e9a3acccd3d
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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