Triethylamine → HCID 117899559, compound

HRID 926995Notes

Reaction equation

HRID 926995 reaction equation
I[C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:17][CH:18]([CH3:21])[C:19]#[CH:20]>CN(C=O)C.[Cu]I.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>[CH3:17][CH:18]([CH3:21])[C:19]#[C:20][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 290124-Iodobenzyl alcoholHCID 690193-Methylbut-1-yne

Product 1

HCID 117899559HCID 117899559, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

4-Iodobenzyl alcohol (1.00 g) was dissolved in DMF (17 mL), added with copper (1) iodide (97.7 mg), triethylamine (0.89 mL), and 3-methyl-1-butyne (1.27 mL), and stirred for 10 minutes in argon atmosphere. Subsequently, it was added with bis(triphenylphosphine)palladium (II) chloride (300 mg) and stirred for 4.3 hours at room temperature in argon atmosphere. After filtration through Celite, it was washed with ethyl acetate and the solvent was evaporated under reduced pressure. The residues were purified by silica gel column chromatography (6 to 40% ethyl acetate/hexane) to obtain the title compound as a yellow oil.

Workup

  1. stirringstirred for 4.3 hours at room temperature in argon atmosphere
  2. filtrationAfter filtration through Celite, it
  3. washwas washed with ethyl acetate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residues were purified by silica gel column chromatography (6 to 40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-43ad57d3588148528213ec3f9772fa03
Source dataset
uspto-grants-2016_03
Patent number
US09290440B2

Reaction notes

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