Triethylamine → HCID 22482228, compound

HRID 2120012Notes

Reaction equation

HRID 2120012 reaction equation
[Br:1][CH:2]([CH3:12])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8](I)=[CH:7][CH:6]=1.[CH2:13]([OH:17])[CH2:14][C:15]#[CH:16].CCN(CC)CC>ClCCl.[Cu]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>[Br:1][CH:2]([CH3:12])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:16]#[C:15][CH2:14][CH2:13][OH:17])=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 135663-Butyn-1-OLHCID 22482249HCID 22482249, compound

Product 1

HCID 22482228HCID 22482228, compoundYield 31.7%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-Bromopropoxy)-1-iodobenzene (10 g, 29 mmol), 3-butyn-1-ol (2.6 mL, 37 mmol), CuI (980 mg, 5.2 mmol) and dichlorobis(triphenylphosphine)palladium(II) (3.6 g, 5.2 mmol) in dichloromethane (40 mL) was added Et3N (6.0 mL, 44 mmol) dropwise. The reaction was stirred overnight at room temperature under Ar. The solvent was evaporated under reduced pressure and ethyl acetate was added to dissolve the compound, the solution was filtered over celite to remove most of the Pd. The crude product was purified by silica gel chromatography, eluted with hexane/ethyl acetate (2:1). 2.6 g of the title compound were obtained as a light brown solid.

Workup

  1. customThe solvent was evaporated under reduced pressure and ethyl acetate
  2. additionwas added
  3. dissolutionto dissolve the compound
  4. filtrationthe solution was filtered over celite
  5. customto remove most of the Pd
  6. customThe crude product was purified by silica gel chromatography
  7. washeluted with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-2c51c6a65384492abf615de3bfcbf17b
Source dataset
uspto-grants-2004_02
Patent number
US06686502B1

Reaction notes

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