Propargyl alcohol → HCID 18467037, compound

HRID 1096734Notes

Reaction equation

HRID 1096734 reaction equation
[CH2:1]([OH:4])[C:2]#[CH:3].I[C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.C(N(CC)CC)C>O1CCCC1.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)I>[CH:12]1[C:13]2[C:8](=[CH:7][CH:6]=[CH:15][CH:14]=2)[CH:9]=[CH:10][C:11]=1[C:3]#[C:2][CH2:1][OH:4]

Participants

7

Reactant 3

HCID 7859Propargyl alcoholHCID 8471TriethylamineHCID 136412beta-Iodonaphthalene

Product 1

HCID 18467037HCID 18467037, compoundYield 11%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

Bis(triphenylphosphine)palladium (II) chloride (0.18 g, 0.26 mmol, 0.18 mol %) was added to a stirred solution of propargyl alcohol (8.43 mL, 144.8 mmol, 1 eq.), 2-iodonapthalene (36 g, 142 mmol), triethylamine (39.6 mL, 284 mmol, 2 eq.) and copper iodide (0.09 g, 0.49 mmol, 0.3 mol %) in tetrahydrofuran (750 ml). The mixture was stirred at 35° C. for 12 h under nitrogen atmosphere. The mixture was then filtered through a bed of celite and the filtrate was washed with ethyl acetate (200 ml). The filtrate was then concentrated in vacuo. Purification by silica gel chromatography using 1:6 ethyl acetate/petrol as the eluting solvent afforded the desired compound (2.85 g, 11%) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 4.54 (2H, s, CH2), 7.45-7.49 (3H, m, ArH), 7.75-7.81 (3H, m, ArH), 7.95 (1H, s, ArH).

Workup

  1. filtrationThe mixture was then filtered through a bed of celite
  2. washthe filtrate was washed with ethyl acetate (200 ml)
  3. concentrationThe filtrate was then concentrated in vacuo
  4. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-a2d143882e97470fac853802a5ee15be
Source dataset
uspto-grants-2012_03
Patent number
US08138377B2

Reaction notes

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